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[ CAS No. 42252-34-6 ] {[proInfo.proName]}

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Chemical Structure| 42252-34-6
Chemical Structure| 42252-34-6
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Product Details of [ 42252-34-6 ]

CAS No. :42252-34-6 MDL No. :MFCD08061404
Formula : C4H8ClNO Boiling Point : -
Linear Structure Formula :- InChI Key :XZVYDRLPXWFRIS-UHFFFAOYSA-N
M.W : 121.57 Pubchem ID :11240471
Synonyms :

Calculated chemistry of [ 42252-34-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 7
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.75
Num. rotatable bonds : 2
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 29.62
TPSA : 20.31 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.23 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.77
Log Po/w (XLOGP3) : 1.15
Log Po/w (WLOGP) : 1.3
Log Po/w (MLOGP) : 0.89
Log Po/w (SILICOS-IT) : 0.18
Consensus Log Po/w : 1.06

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.19
Solubility : 7.92 mg/ml ; 0.0651 mol/l
Class : Very soluble
Log S (Ali) : -1.17
Solubility : 8.2 mg/ml ; 0.0674 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.91
Solubility : 14.9 mg/ml ; 0.122 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.04

Safety of [ 42252-34-6 ]

Signal Word:Danger Class:8
Precautionary Statements:P501-P260-P234-P264-P280-P390-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338-P310-P406-P405 UN#:3265
Hazard Statements:H314-H290 Packing Group:Ⅱ
GHS Pictogram:

Application In Synthesis of [ 42252-34-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 42252-34-6 ]

[ 42252-34-6 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 42252-34-6 ]
  • [ 105601-04-5 ]
  • [ 105601-20-5 ]
YieldReaction ConditionsOperation in experiment
66% With potassium carbonate; In acetonitrile; at 70 - 80℃; Condensation reaction of 3-(l-dimethylaminoethyl) phenol (10 gm) and ethylmethylcarbamoyl chloride (10gm) was carried in the presence of potassium carbonate (25 gm) and acetonitrile (150 ml) at 70-80 C. After completion of reaction, the reaction mixture was quenched in water (250 ml) at 30-35 C and extracted in ethyl acetate (100ml). Evaporation of ethyl acetate gave the desired compound in 70% yield. Yield: 80-85 gms. %Yield: 66.0% HPLC Purity: 99%.
b) Preparation of 3-(1-(dimethylamino)ethyl)phenyl ethyl-(methyl) carbamate (rivastigmine base) An amount of 5.25 g (30.0 mmol) of 3-(1-dimethylaminoethyl)-phenol was dissolved in 70 ml of acetonitrile. To the solution was slowly added 1.30 g (32.5 mmol) of sodium hydride and stirred for 30 minutes. 6.20 g (51 mmol) of ethyl(methyl)-carbamic chloride were slowly added to the solution. The reaction mixture was stirred for 20 hours. The mixture was filtered and concentrated. 100 ml of water were added and the pH was adjusted with 0.1 M NaOH to pH 12, followed by extraction with ether (3x100 ml). The organic layer was then washed with 100 ml of brine, dried over sodium sulfate, filtered and concentrated. 6.20 g of an oily residue of rivastigmine base were obtained.
An amount of 1.1 g (27.5 mmol, 60 %, 1.05 mole) of sodium hydride suspended in 15 ml of acetonitrile was added to 1.0 mole of the above obtained 3-(1-dimethylaminoethyl)phenol (as acetonitrile solution) within a period of 30 minutes while maintaining the reaction mixture at the room temperature. After the addition of sodium hydride an amount of 3.1 ml (3.44 g, 97 % 27.5 mmol, 1.05 molar equivalent) of ethyl(methyl)-carbamic chloride were added within a period of 30 minutes. The reaction mixture was stirred for 2 hours at room temperature and then the solvent was removed under vacuum at 50 mbar and 50C. 55 ml of ether and 35 ml of water were added to the residue, the pH was set to 11 with 0.1 M NaOH and stirred for 20 minutes. The layers were separated. The water phase was washed with 25 ml of ether and the organic phases were combined, dried with 2.0 g of Na2SO4 and filtered. The filtrate was concentrated to obtain 6.4 g of an oily substance of 3-(1-(dimethylamino)ethyl)phenyl ethyl(methyl)carbamate. Yield from 1-(3-hydroxyphenyl)-N,N-dimethyl-ethanaminium chloride was 85 %, purity of the product 97.7 area %.
  • 2
  • [ 42252-34-6 ]
  • [ 129150-68-1 ]
  • [ 209546-54-3 ]
  • 3
  • [ 42252-34-6 ]
  • [ 123441-03-2 ]
YieldReaction ConditionsOperation in experiment
86.6% 150 ml of diethylether are placed in a 0.51-three-neck flask and sodium hydride as a 60% dispersion in oil (0.48 g) is added slowly under inert conditions (Ar or N2) and stirring. A suspension develops, to which crystalline compound (III) (2.0 g, 0.012 mol) is added at room temperature. After stirring for one hour, a slightly turbid solution of the phenolate forms, to which 1.53 g (0.012 mol) OF N-ETHYL-N-METHYLCARBAMOYLCHLORIDE in 20 ml of ether are added dropwise at room temperature. The resulting reaction mixture is stirred at room temperature for 3 hours. Thereafter, it is diluted with 100 ml of water. The organic layer is separated and extracted with 2x 50 ml of a 0.1 N NAOH solution. The organic phase is extracted with 50 ml of water, dried with anhydrous magnesium sulfate, and concentrated in vacuo. 2.6 g of an oil are obtained (86.6% of the theoretical yield).
80.5% 300 ml of tetrahydrofuran (THF) are placed in a 0.51-three-neck flask and sodium hydride as a 60% dispersion in oil (11.3 g) is added slowly under inert conditions (Ar or N2) and stirring. A suspension develops, to which crystalline compound (III) (46.5 g, 0.281 mol) is added at room temperature. A solution of the phenolate forms, to which 35.7 g (0.281 mol) of carbamoylchloride are added dropwise over 10 minutes while slightly cooling down to 15 C. The reaction is slightly exothermic. The rate of dropping is kept such that the temperature of the reaction mixture does not exceed 30 C. After all the agent is added, the cooling system is put aside and the reaction mixture is mixed for 2 hours at room temperature. Thereafter, THF is evaporated in a rotary vacuum evaporator. The evaporation residue is partitioned between 200 ml 1N NAOH and 500 ml of ether. The organic layer is separated and the aqueous fraction is shaken with additional 2x 200 ml of ether. The combined ether layers are shaken out with lx 100 ml water and lx 50 ml brine. The organic fraction is dried over anhydrous sodium sulfate. The solvent is evaporated and the crude product is vacuum distilled. b. p. = 135-140 C at 13 Pa 45.6 g of a colorless viscous oil are obtained, i. e. a 80.5% yield. content GC 99.6%
80.5% Reference example 1: Preparation of S-(-)-Rivastigmine; 300ml of tetrahydrofuran (THF) are placed in a 0.51 -three-neck flask and sodium hydride as a 60% dispersion in oil (11.3g) is added slowly under inert conditions (Ar or N2) and stirring. A suspension develops, to which alpha-m-hydroxy phenylethyldimethylamine (46.5g, 0.28 lmol) is added at room temperature. A solution of the phenolate forms, to which 35.7g (0.28 lmol) of carbamoylchloride are added dropwise over 10 minutes while slightly cooling down to 150C. The reaction is slightly exothermic. The rate of dropping is kept such that the temperature of the reaction mixture does not exceed 30C. After all the agent is added, the cooling system is put aside and the reaction mixture is mixed for 2 hours at room temperature. Thereafter, THF is evaporated in a rotary vacuum evaporator. The evaporation residue is partitioned between 200 ml IN NaOH and 500 ml of ether. The organic layer is separated and the aqueous fraction is shaken with additional 2x 200 ml of ether. The combined ether layers are shaken out with Ix 100 ml water and Ix 50 ml brine. The organic fraction is dried over anhydrous sodium sulfate. The solvent is evaporated and the crude product is vacuum distilled. b. p. =135-140oC at l3 Pa 45.6 g of a colorless viscous oil are obtained, i.e. a 80.5% yield. Content GC 99.6%
51.5% 50 ml 1,2-dimethoxyethane are placed in a 0.251 round three-neck flask and compound (III) (2.0 g, 0.012 mol) is dissolved therein under stirring and under an inert (Ar or N2) at room temperature. Then, a 1.6M solution of n-butyllithium in hexane (7.5 ml) is added dropwise to the resulting solution. A slightly turbid solution of the phenolate develops, to which 1.53 g (0.012 mol) of N-ethyl-N-methylcarbamoylchloride in 20 ml of 1,2-dimethoxyethane are added dropwise at room temperature. The solvent is evaporated in a rotary vacuum evaporator. The evaporation residue is partitioned between 20 ml 1N NAOH and 50 ML of ether. The organic layer is separated and the aqueous fraction is shaken with additional 2x 20 ml of ether. The combined ether layers are shaken with lx 20 ml water and lx 20 ml brine. The organic fraction is dried over anhydrous sodium sulfate and concentrated in vacuo. 1.56 g of an oil are obtained (51.5% of the theoretical yield).

  • 4
  • [ 42252-34-6 ]
  • [ 105601-04-5 ]
  • [ 105601-14-7 ]
YieldReaction ConditionsOperation in experiment
58% [80] alpha-m-Hydroxyphenylethyldimethylamine (Formula 2, 50.0 g, 0.3 mol) was suspended in acetonitrile (250 ml), and then N-ethyl-N-methylcarbamoyl chloride (58.3 g, 0.48 mol) was added thereto. The reaction solution was cooled to 0C. To the cooled solution was added sodium hydroxide (14.4 g, 0.36 mol). The resulting mixture was gradually allowed to rise to room temperature, and stirred at this temperature for 24 hours. The completion of the reaction was confirmed by HPLC. Thereafter, the reaction mixture was filtered to remove salts, and the obtained filtrate was concentrated. The pH of the concentrate was adjusted to 11 using water and NaOH solution, followed by extraction with ether and concentration. To the concentrate were added water and cone. HCl. The mixture was stirred at room temperature for one hour, and washed twice with ether. The obtained aqueous layer was concentrated, and re- crystallized from ethylacetate, yielding racemic rivastigmine hydrochloride (50.6 g, 58%). The racemic rivastigmine hydrochloride (20 g, 69 mmol) was dissolved in water (60 ml), and then NaOH (3.3 g, 1.2 eq.) was added thereto. The mixture was stirred at room temperature for one hour. The resulting mixture was extracted five times with ether, dried over anhydrous MgSO , and concentrated under reduced pressure. Di-O, O'4-p-toluoyl tartaric acid monohydrate (DTTA, 26.5 g, 69 mmol) and a solution of methanol/water (2/1) (180 ml) were added to the concentrate, dissolved under heating, and gradually allowed to cool to room temperature to obtain a precipitate. The precipitate was filtered, and recrystallized four times to afford rivastigmine DTTA salt (11.4 g, 26% (from the racemic rivastigmine hydrochloride)). The obtained rivastigmine DTTA salt (4.7 g, 7.4 mmol) was suspended in a IM NaOH solution (8 ml) EPO <DP n="10"/>and dichloromethane (30 ml). The suspension was stirred for 30 minutes, followed by phase separation. The obtained organic layer was concentrated, and water and ether were added to the concentrate to separate layers. The obtained ether layer was dried over K CO , and concentrated. To the concentrate were added acetone (5 ml) and L- tartaric acid (1.1 g, 7.4 mmol, 1 eq.). The resulting mixture was refluxed for one hour, cooled to 0C, and filtered to obtain a solid. The solid was washed, and dried to afford (S)-rivastigmine tartrate salt (2.5 Ig, 99.7% ee, 85% (from the rivastigmine DTTA salt), 13% (from the alpha-m-hydroxyphenylethyldimethylamine).
  • 5
  • [ 42252-34-6 ]
  • [ 139306-10-8 ]
  • [ 123441-03-2 ]
YieldReaction ConditionsOperation in experiment
80.5% Reference Example 1Preparation of S-(-)-Rivastigmine300 ml of tetrahydrofuran (THF) are placed in a 0.51-three-neck flask and sodium hydride as a 60% dispersion in oil (11.3 g) is added slowly under inert conditions (Ar or N2) and stirring. A suspension develops, to which alpha-m-hydroxy phenylethyldimethylamine (46.5 g, 0.281 mol) is added at room temperature. A solution of the phenolate forms, to which 35.7 g (0.281 mol) of carbamoylchloride are added dropwise over 10 minutes while slightly cooling down to 15 C. The reaction is slightly exothermic. The rate of dropping is kept such that the temperature of the reaction mixture does not exceed 30 C. After all the agent is added, the cooling system is put aside and the reaction mixture is mixed for 2 hours at room temperature. Thereafter, THF is evaporated in a rotary vacuum evaporator. The evaporation residue is partitioned between 200 ml IN NaOH and 500 ml of ether. The organic layer is separated and the aqueous fraction is shaken with additional 2×200 ml of ether. The combined ether layers are shaken out with 1×100 ml water and 1×50 ml brine. The organic fraction is dried over anhydrous sodium sulfate. The solvent is evaporated and the crude product is vacuum distilled.b.p.=135-140 C. at 13 Pa45.6 g of a colorless viscous oil are obtained, i.e. a 80.5% yield. Content GC 99.6%
74% With potassium carbonate; In acetonitrile; (S)-3-(l-dimethylaminoethyl) phenol (V-a; 25gm; 0.15mole) was reacted with Ethyl methyl carbamoyl chloride (20gm, 0.165 mole) in presence of anhydrous.potassium carbonate (31.5 gm, 0.228 moles) and acetonitrile (250ml) and heated. After completion of reaction the reaction mixture was filtered and the filtrate concentrated to give product. The product was optionally purified by acid base treatment. Yield: 27 gmYield: 74%Purity: 99% (by HPLC)
With pyridine;tetrabutylammomium bromide; In 4-methyl-2-pentanone; at 30℃; for 15.75h; EXAMPLE 5: PREPARATION OF (S)-N-ETHYL-N-METHYL-3-[1-DIMETHYL-AMINO)-ETHYL]-PHENYL CARBAMATE (FORMULA II); . 6 kg of S-(-)-[1-(3-hydroxyphenyl) ethyl] dimethyl amine of Formula III and 12 L of Methyl Isobutyl Ketone(MIBK) were charged and stirred for about 10 minutes. To this reaction solution 3.44 kg of pyridine, 1.18 kg of tetrabutylammonium bromide were charged and stirred for about 15 minutes to form clear solution. 3.97 kg of N-ethyl, N-methyl carbomyl chloride was added to the reaction mixture for about 30 minutes. Heated the contents to about 30C and stirred for about 15 hours. After completion of the reaction 48 lit of water was charged and pH was adjusted to about 1.5 using 3.72 lit of 36% aqueous hydrochloric acid. Stirred the contents for about 30 minutes at about 25C and aqueous layer was separated. The aqueous layers were then washed with MIBK (2x12 lit) and separate the aqueous layer. Aqueous layer pH was adjusted to 12.5 using 6 lit of 40% aqueous sodium hydroxide solution and stirred for about 15 minutes. The aqueous layer was then extracted with MIBK (2x12 lit) and separated the organic layer. Washed the organic layer with water (2x12 lit) and separated the organic layer. The obtained organic layer was distilled off completely at about 60C to afford residue. To the obtained residue 48 lit of ethyl acetate was added and pH of the reaction solution was adjusted to about 2 by adding about 6 lit of f 18% hydrochloride in isopropyl alcohol at about 5C and stirred for about 90 minutes for solid separation. The separated solid was filtered and washed with 6 lit of ethyl acetate. The obtained wet solid was again charged into a reaction containing 30 lit of water and adjusted the pH to about 12.5 using 1.8 lit of 40% aqueous sodium hydroxide solution(caustic lye). The reaction mass was extracted with MIBK (2x12 lit) and the combined organic layer was washed with water (2x12 lit). The organic layer was distilled completely at about 60C to afford residue. To the obtained residue 48 lit of ethyl acetate was added and pH of the reaction solution was adjusted to about 2 by adding about 6 lit of f 18% hydrochloride in isopropyl alcohol at about 5C and stirred for about 90 minutes for solid separation. The separated solid was filtered and washed with 6 lit of ethyl acetate. The obtained wet solid was again charged into a reaction containing 30 lit of water and adjusted the pH to about 12.5 using 1.8 lit of 40% aqueous sodium hydroxide solution. The reaction mass was extracted with MIBK (2x12 lit) and the combined organic layer was washed with water (2x121it). The organic layer was distilled completely at about 60C to afford the title compound Purity by HPLC. 99.33%
With pyridine;tetrabutylammomium bromide; In 4-methyl-2-pentanone; at 30℃; for 15.75h; Example 5; Preparation of (S)-N-Ethyl-N-Methyl-3-[1-Dimethyl-Amino)-Ethyl]-Phenyl Carbamate (Formula II); 6 kg of S- (-)-[1-(3-hydroxyphenyl)ethyl] dimethyl amine of Formula III and 12 L of Methyl Isobutyl Ketone(MIBK) were charged and stirred for about 10 minutes. To this reaction solution 3.44 kg of pyridine, 1.18 kg of tetrabutylammonium bromide were charged and stirred for about 15 minutes to form clear solution. 3.97 kg of N-ethyl, N-methyl carbornyl chloride was added to the reaction mixture for about 30 minutes. Heated the contents to about 30 C. and stirred for about 15 hours. After completion of the reaction 48 lit of water was charged and pH was adjusted to about 1.5 using 3.72 lit of 36% aqueous hydrochloric acid. Stirred the contents for about 30 minutes at about 25 C. and aqueous layer was separated. The aqueous layers were then washed with MIBK (2×12 lit) and separate the aqueous layer. Aqueous layer pH was adjusted to 12.5 using 6 lit of 40% aqueous sodium hydroxide solution and stirred for about 15 minutes. The aqueous layer was then extracted with MIBK (2×12 lit) and separated the organic layer. Washed the organic layer with water (2×12 lit) and separated the organic layer. The obtained organic layer was distilled off completely at about 60 C. to afford residue.To the obtained residue 48 lit of ethyl acetate was added and pH of the reaction solution was adjusted to about 2 by adding about 6 lit of 18% hydrochloride in isopropyl alcohol at about 5 C. and stirred for about 90 minutes for solid separation. The separated solid was filtered and washed with 6 lit of ethyl acetate. The obtained wet solid was again charged into a reaction containing 30 lit of water and adjusted the pH to about 12.5 using 1.8 lit of 40% aqueous sodium hydroxide solution (caustic lye). The reaction mass was extracted with MIBK (2×12 lit) and the combined organic layer was washed with water (2×12 lit). The organic layer was distilled completely at about 60 C. to afford residue.To the obtained residue 48 lit of ethyl acetate was added and pH of the reaction solution was adjusted to about 2 by adding about 6 lit of 18% hydrochloride in isopropyl alcohol at about 5 C. and stirred for about 90 minutes for solid separation. The separated solid was filtered and washed with 6 lit of ethyl acetate. The obtained wet solid was again charged into a reaction containing 30 lit of water and adjusted the pH to about 12.5 using 1.8 lit of 40% aqueous sodium hydroxide solution. The reaction mass was extracted with MIBK (2×12 lit) and the combined organic layer was washed with water (2×12 lit). The organic layer was distilled completely at about 60 C. to afford the title compound.Purity by HPLC. 99.33%
Example 6; Preparation of Rivastigmine25 gm of S-(-)-3-[(l-dimethylamino) ethylj-phenol was dissolved in 250 ml of THF and 12.5 gm of KOH was charged in a flask and stirred for 10 minutes. The reaction mixture was cooled to 10-15C under nitrogen atmosphere. 25 gm of N-methyl, N-ethyl carbamoyl chloride was added slowly for about 30 minutes and then stirred for 30 minutes. The reaction mixture temperature was allowed to 25-35 and stirred for about 5 hours. The reaction mixture was charged into a flask containing 200 ml of water which is cooled to 0-5C. The reaction mixture was extracted with toluene (200 ml). Total organic layer was extracted with 20 % aqueous HCl solution. The aqueous layer pH was adjusted to about 10 using aqueous sodium hydroxide solution. The aqueous layer was extracted with dichloromethane (200 ml). The total dichloromethane layer was washed with water and distilled off completely to get 34 gm of rivastigmine base.
77.1 g With sodium hydride; In tetrahydrofuran; at 0 - 20℃; for 3h; 2L of tetrahydrofuran was added to the reaction flask, and 100 g of Intermediate 1 was dissolved with stirring. The ice-water bath was cooled to 13 C. and 30 g of sodium hydride was slowly added in portions. After the addition is completed, it is cooled to 0C. A solution of 80 g of N-ethyl-N-methylcarbamoyl chloride in tetrahydrofuran (80 g of N-ethyl-N-methylcarbamoyl chloride dissolved in 160 ml of tetrahydrofuran) was added dropwise, and the mixture was naturally heated toAt room temperature, the reaction was stopped for 3 hours. After the reaction was completed, 100 ml of water was slowly added to quench the reaction. The tetrahydrofuran was concentrated under reduced pressure, 800 ml of water was added to the system, pH was adjusted to 3.5 with concentrated hydrochloric acid, and dichloromethane (500 ml) was washed with 3*3. The organic layer was discarded. The aqueous phase was extracted with 2M NaOH solution adjusted to pH 11,600 ml*2 dichloromethane and the aqueous phase was discarded. The methylene chloride layer was washed once with 1 M sodium hydroxide solution, twice with water, and once with saturated brine. The dichloride layer was collected and concentrated to obtain 77.1 g of a pale yellow oil.
Example-8: Preparation of Rivastigmine Base To a 100 ml. RB flask, MDC (5 ml), and NaH (0.36 g) were added. To the above reaction mixture, a solution of (1S)-3-(1-Dimethylamino-ethyl)-phenol (1.0 g) in MDC (15 ml) was added drop wise at 20-25 C. for about 5 min and followed by added drop wise N-Ethyl N-methyl carbamoyl chloride (0.88 g) at 20-25 C. for about 5 min. Heated the reaction mass to reflux for 4 to 5 hours and cooled to room temperature. Added DM water (5 ml) followed by adjusted the pH 1 to 2 by dil. HCl. Layers were separated and MDC layer was extracted with DM water (5 ml*2). Collected and combined all aqueous layers, basify the pH 12 to 13 with 25% KOH. Extracted the compound in EtOAc (5 ml) and evaporated to dryness to obtained 1.18 g of Rivastigmine base (Yield: 77.8%, HPLC: 91.42%, Chiral HPLC: 98.09%).

  • 6
  • [ 42252-34-6 ]
  • [ 105601-04-5 ]
  • [ 123441-03-2 ]
YieldReaction ConditionsOperation in experiment
97.6% With sodium carbonate; In acetone; for 8h; (1) is added to the three-port flask 3 - (1 - (dimethyl-amino) ethyl) phenol (19.8g, 0 . 12mol) and acetone 130 ml, by adding 4.5g anhydrous sodium carbonate activated for a certain time, by adding Kabool carbamic chloride (15.9g, 0 . 13mol), reaction 8 hours, after recycling of acetone, adding dichloromethane 110 ml and water 150 ml, using hydrochloric acid to adjust pH to 3, extraction, removed the organic phase, the water layer by adding 150 ml dichloromethane, adding concentrated ammonia to pH 10, separating an aqueous layer, 100 mi washing organic phase, from the solvent by reduced pressure evaporation to dryness methylene chloride level, of free alkali to get the yellow liquid of Rivastigmine 29.3g, yield 97.6%.
  • 7
  • [ 42252-34-6 ]
  • [ 436-77-1 ]
  • 7-O-(ethyl(methyl)carbamyl) fangchinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With dmap; In dichloromethane; at 0 - 20℃;Inert atmosphere; General procedure: Acyl chloride (0.18 mmol, 1.1 eq) was added at 0 C to a solution of <strong>[436-77-1]fangchinoline</strong> (100 mg, 0.16 mmol) and DMAP (0.032 mmol, 0.2eq) in 2 mL dry CH2Cl2 under argon and stirred for 2-4 h. The reaction mixture was quenched with a saturated aqueous solution of sodium bicarbonate and extracted three times with CH2Cl2. The combined organic phase was dried over anhydrous magnesium sulfate before vacuum suction filtration. The removal of the solventin vacuo afforded the crude product, which was chromatographied on silica gel (CH2Cl2/MeOH, 50/1 v/v, 0.1% TEA) to provide the pureproduct 1a-1e, 2a-2g, 3a-3e and 4a-4h.
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; ;