[ CAS No. 13889-98-0 ] {[proInfo.proName]}

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2D 3D

Structure of 13889-98-0 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 13889-98-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 13889-98-0 ]

SDS Specification

Alternatived Products of [ 13889-98-0 ]

Product Details of [ 13889-98-0 ]

CAS No. :	13889-98-0	MDL No. :	MFCD00058676
Formula :	C₆H₁₂N₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PKDPUENCROCRCH-UHFFFAOYSA-N
M.W :	128.17	Pubchem ID :	83795
Synonyms :

Calculated chemistry of [ 13889-98-0 ] Expand+

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.83
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	42.57
TPSA :	32.34 ?2

Pharmacokinetics

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.74 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.51
Log Po/w (XLOGP3) :	-0.93
Log Po/w (WLOGP) :	-1.32
Log Po/w (MLOGP) :	-0.41
Log Po/w (SILICOS-IT) :	0.35
Consensus Log Po/w :	-0.16

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	0.02
Solubility :	133.0 mg/ml ; 1.04 mol/l
Class :	Highly soluble
Log S (Ali) :	0.73
Solubility :	696.0 mg/ml ; 5.43 mol/l
Class :	Highly soluble
Log S (SILICOS-IT) :	-0.67
Solubility :	27.2 mg/ml ; 0.212 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.12

Safety of [ 13889-98-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362+P364-P403+P233-P501	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 13889-98-0 ]

* 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.

Upstream synthesis route of [ 13889-98-0 ]
Downstream synthetic route of [ 13889-98-0 ]

[ 13889-98-0 ] Synthesis Path-Upstream 1~1

1
[ 13889-98-0 ]
[ 1374640-70-6 ]

Reference： [1] Patent: CN105461640, 2016, A,
[2] Patent: CN105461640, 2016, A,

[ 13889-98-0 ] Synthesis Path-Downstream 1~10

1
[ 13889-98-0 ]
[ 2207-32-1 ]
C₁₂H₁₄N₄OS [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 3988 - 3991

2
[ 13889-98-0 ]
[ 71831-21-5 ]
[ 1072120-10-5 ]

Yield	Reaction Conditions	Operation in experiment
70%	With sodium hydrogencarbonate; In dichloromethane; at 23 - 30℃; for 15.1667h;	Example 3Preparation of intermediate (Va where n=l and R= acetyl) 4-(4-acetyl-piperazin- 1 -yl-methy lpheny Dmethano 15.5 volumes of Toluene were loaded in a glass lined vessel under N2 and cooled down to -200C +/- 2°C.In a separate vessel, 1.5 kg of methyl-4-bromo-methylbenzoate were charged portion wise while stirring under N2 at room temperature to obtain a solution (solution B).19.8 liters (3.02 eq.) of a 1 M solution DIBAL-H/Toluene under N2 were added, cooling down the solution to -200C +/- 2°C and stirring.The solution B was loaded under N2 portion wise while maintaining the temperature in the range 0-150C (< 350C) by addition over about 1 hour.Reaction was monitored by HPLC when addition was completed. The mixture was cooled down to -200C +/- 2°C under stirring.8.8 volumes (2.02 eq.) of IM acq. HCl (cooled to 5°C +/- 2°C) were added drop wise under very slow stirring and maintaining the temperature below 300C (<35°C).Stirring was stopped and phases separated at 8°C +/- 2°C. Water phase was removed.5 volumes Of H2O were then charged, maintaining the temperature at 100C +/- 2°C, very slowly stirring was done for a further 10 minutes.Stirring was stopped and phases separated at 100C +/- 2°C, then removed. Washing with water and phase separation were repeated. <n="14"/>Toluene was removed by distillation under reduced pressure maintaining solution temperature at 35°C (< 400C) to obtain a white solid with yield equal to 90percent.The above solid is dissolved in 7 volumes of dichloromethane in a vessel under N2 stirring at 25°C for about 15 minutes. In a separate vessel, 1.05 kg of N-acetyl- piperazine were dissolved in 3 volumes of dichloromethane stirring at 25°C.Sodium bicarbonate was charged portion wise to the dichloromethane solution under stirring at 23°C +/- 2°C in about 10 minutes.N-acetyl-piperazine solution was loaded to dichlorometane-bicarbonate mixture under stirring at 300C +/- 2°C. The mixture was stirred at that temperature for 15 hours, monitoring the reaction by HPLC.The reaction mixture was cooled down at 23°C +/- 2°C.2 volumes of water were added under stirring at 25°C for about 15 minutes. Stirring was stopped and the phases were separated. Organic phases were separated.Organic phases were washed with water (2 x 2 volumes) under stirring for 15 minutes at 25°C. Water phases were collected and washed (2 x 3 volumes) with dichloromethane under stirring for 15 minutes at 25°C. Organic phases were removed, collected and dried over anhydrous sodium sulfate. The solid cake was washed with 2 volumes of dichloromethaneDichloromethane solution was concentrated (about 15 volumes at 400C under vacuum), subsequently 6 volumes of ethyl acetate were added.6 volumes of solvent were removed at 65°C.The solution was cooled down to 53°C in about 1 hour under slow stirring, then to 5°C +/- 2°C in about 2.5 hours under slow stirring to obtain crystallization of the material.The mixture was filtered at 5°C and the solid cake washed with 1 volume of ethyl acetate (cooled at 5°C).A second crop of material could be obtained from mother liquors by concentration and cooling. <n="15"/>The solid was dried in vacuo in oven (30°C+/-2°C) for about 15 hours.Average yield 70percent (wt) starting from methyl-4-bromo-methylbenzoate, average purity for this step (> 97percent) on 13 batches.

Reference： [1]Patent: WO2008/125518,2008,A2 .Location in patent: Page/Page column 12-14

3
[ 13889-98-0 ]
[ 28987-44-2 ]
1-(4-(3-ethoxy-4-nitrophenyl)piperazin-1-yl)ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 80℃;	Step 2: Preparation of 1-(4-(3-ethoxy-4-nitrophenyl)piperazin-1-yl)ethanone The compound obtained in Step 1 above (300 mg), N-acetylpiperazine (300 mg), and potassium carbonate (500 mg) were dissolved in dimethylformamide (3 mL) and reacted at 80C overnight. The dimethylformamide of the reaction mixture was removed under reduced pressure, and added with water to form a solid. The solid was filtered to obtain a target compound as a yellow solid. 1H-NMR(300 MHz, CDCl3) δ 7. 97 (d, J = 9.3 Hz, 1H), 6.40(dd, J = 2.5, 9.3 Hz, 1H), 6.32(d, J = 2.5 Hz, 1H), 4.15(q, J = 7.0 Hz, 2H), 3.79(m, 2H), 3.66(m, 2H), 3.40(m, 4H), 2.15(s, 3H), 1.50(t, J = 7.0 Hz, 3H).
	With potassium carbonate; In N,N-dimethyl-formamide; at 80℃;	The compound obtained in Step 1 above (300 mg), N-acetylpiperazine (300 mg), and potassium carbonate (500 mg) were dissolved in dimethylformamide (3 mL) and reacted at 80 C. overnight. The dimethylformamide of the reaction mixture was removed under reduced pressure, and added with water to form a solid. The solid was filtered to obtain a target compound as a yellow solid. [0190]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 6192 - 6196
[2]Patent: EP2883875,2015,A1 .Location in patent: Paragraph 0069
[3]Patent: US2015/152069,2015,A1 .Location in patent: Paragraph 0189; 0190

4
[ 13889-98-0 ]
[ 2106-50-5 ]
1-(4-(3-chloro-4-nitrophenyl)piperazin-1-yl)ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 50℃;	Step 1: Preparation of 1-(4-(3-chloro-4-nitrophenyl)piperazin-1-yl)ethanone <strong>[2106-50-5]2-chloro-4-fluoronitrobenzene</strong>(350 mg), N-acetylpiperazine (0.5 ml) and potassium carbonate (500 mg)were dissolved in dimethylformamide (3 ml) and stirred at 50C overnight. The reaction mixture was distilled under reduced pressure to remove dimethylformamide and added with distilled water. Then, the recrystalized yellow solid was filtered and the subsequent reaction was proceeded without further purification. 1H NMR (300 MHz, CDCl3) delta 8.04(d, J = 9.3 Hz, 1H), 6.86(d, J = 2.0 Hz, 1H), 6.74(dd, J = 2.0, 9.3 Hz, 1H), 3.80(m, 2H), 3.66(m, 2H), 3.42(m, 4H), 2.16(s, 3H).
	With potassium carbonate; In N,N-dimethyl-formamide; at 50℃;	<strong>[2106-50-5]2-chloro-4-fluoronitrobenzene</strong> (350 mg), N-acetylpiperazine (0.5 ml) and potassium carbonate (500 mg) were dissolved in dimethylformamide (3 ml) and stirred at 50 C. overnight. The reaction mixture was distilled under reduced pressure to remove dimethylformamide and added with distilled water. Then, the recrystallized yellow solid was filtered and the subsequent reaction was proceeded without further purification.?H NMR (300 MHz, CDC13) oe 8.04 (d, J=9.3 Hz, 1H), 6.86 (d, J=2.0 Hz, 1H), 6.74 (dd, J=2.0, 9.3 Hz, 1H), 3.80 (m, 2H), 3.66 (m, 2H), 3.42 (m, 4H), 2.16 (s, 3H).

Reference： [1]Patent: EP2883875,2015,A1 .Location in patent: Paragraph 0084
[2]Patent: US2015/152069,2015,A1 .Location in patent: Paragraph 0207; 0208; 0209

5
[ 13889-98-0 ]
[ 2106-50-5 ]
1-(4-(4-amino-3-chlorophenyl)piperazin-1-yl)ethanone [ No CAS ]

Reference： [1]Patent: EP2883875,2015,A1
[2]Patent: US2015/152069,2015,A1

6
[ 13889-98-0 ]
[ 454-16-0 ]
1-(4-(2-methoxy-4-nitrophenyl)piperazin-1-yl)ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 20h;	10302] Preparation of 1 -(4-(2-methoxy-4-nitrophenyl)pip- erazin- 1 -yl)ethanone: A mixture of 1 -fluoro-2-methoxy-4- nitrobenzene (0.83 g, 4.9 mmol), 1-acetylpiperazine (0.68 g, 5.3 mmol), and potassium carbonate (1.3 g, 9.7 mmol) in N,N-dimethylformamide (9 mE) was stirred at 100°C. for 20 hours. The mixture was allowed to cool to room temperature and was partitioned between ethyl acetate and watet The aqueous phase was extracted three times with ethyl acetate. The combined extracts were washed twice with water, once with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, filtered, and concentrated to provide the desired material. ECMS-ESI (mlz): [M+H] calcd for C,3H,8N304: 280.1. found: 280.1 Preparation of 1 -(4-(4-amino-2-methoxyphenyl)piperazin-1 -yl)ethanone:A degassed mixture of 1 -(4-(2-methoxy-4-nitrophenyl)pip- erazin-1 -yl)ethanone (approximately 4.9 mmol) in methanol 2-methyltetrahydrofuran (1:1, 60 mE) was treated with 10percent palladium on charcoal (250 mg). The mixture was stirred under a balloon of hydrogen overnight. The catalyst was removed by filtration through a pad of Celite diatomaceous earth. The filtrate was concentrated to dryness under reduced pressure to provide the desired material.

Reference： [1]Patent: US2016/96827,2016,A1 .Location in patent: Paragraph 0302

7
[ 13889-98-0 ]
[ 314298-13-0 ]
1-(4-(5-methoxy-2-methyl-4-nitrophenyl)piperazin-1-yl)ethan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
34%	With potassium carbonate; In N,N-dimethyl-formamide; at 120℃; for 16h;	(0666) 1-Fluoro-5-methoxy-2-methyl-4-nitrobenzene (4.2 g, 22.7 mmol) and 1-(piperazin-1-yl)ethan-1-one (2.9 g, 22.7 mmol) were dissolved in N,N-dimethylformamide (20 mL), and potassium carbonate (6.3 g, 45.4 mmol) was added. The resultant mixture was stirred at 120 C. for 16 h. After the reaction, the mixture was cooled to room temperature. Water (50 mL) was added, and the mixture was extracted with ethyl acetate (50 mL×2). The organic phases were combined, dried, filtrated, concentrated, and purified by silica gel column chromatography (petroleum ether:ethyl acetate=1:2) to get the title compound (2.26 g, yield: 34%).

Reference： [1]Patent: US2017/112833,2017,A1 .Location in patent: Paragraph 0665-0666

8
[ 13889-98-0 ]
[ 118650-08-1 ]
methyl 2-[5-(4-acetylpiperazin-1-yl)pyridin-3-yl]acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
13%	With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; XPhos; In toluene; at 110℃; for 16h;Inert atmosphere;	Step 2: <strong>[118650-08-1]methyl 2-(5-bromopyridin-3-yl)acetate</strong> Ex.12a (303 mg, 1 .32 mmol), 1-(piperazin-1-yl)ethan-1-one (247 muIota_, 1 .98 mmol) and Cs2C03 (644 mg, 1.98 mmol) were charged to a screw cap tube, dry toluene (4 mL) was added and the mixture was degassed by nitrogen bubbling for 5 min. Then Pd2(dba)3 (60 mg, 0.07 mmol) and XPhos (63 mg, 0.13 mmol) were incorporated and the reaction Ex.12b mixture was stirred at 110 C for 16h. The reaction mixture was cooled to r.t, diluted with EtOAc and water. The two phases were separated. The organic layer was dried over MgS04, filtered and the solution was concentrated to dryness. The crude material was purified by column chromatography eluting with a gradient of Heptane/EtOAc from [100:0] to [0:100]. The product fractions were combined and concentrated to dryness to afford methyl 2-[5-(4-acetylpiperazin-1-yl)pyridin-3-yl]acetate Ex.12b (97 mg, 13%) as yellow oil.

Reference： [1]Patent: WO2018/138356,2018,A1 .Location in patent: Page/Page column 35; 45

9
[ 13889-98-0 ]
[ 546-43-0 ]
C₂₁H₃₂N₂O₃ [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,2018,vol. 55,p. 2715 - 2721

10
[ 327056-62-2 ]
[ 13889-98-0 ]
5-(4-acetylpiperazin-1-yl)pyridine-2-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.57 g	With N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; at 80℃; for 0.75h;	Example IX.1 5-(4-Acetylpiperazin-1-yl)pyridine-2-carbonitrile A mixture of 250 mg (2.05 mmol) 5-fluoropyridine-2-carbonitrile (CAS No. 327056-62-2), 310 mg (2.46 mmol) 1-acetylpiperazine (CAS No. 13889-98-0) and 700 μL (4.10 mmol) DIPEA in 3 mL DMSO is stirred at 80 C. for 45 min and quenched with semi conc. NaCl/solution. The water phase is extracted with EtOAc. The combined organic phases are dried via PTK and concentrated in vacuo to give 0.57 g of the product. C12H14N4O (M=230.3 g/mol) ESI-MS: 231 [M+H]+

Reference： [1]Patent: US2021/24495,2021,A1 .Location in patent: Paragraph 0148-0152

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P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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[ CAS No. 13889-98-0 ] {[proInfo.proName]}

Quality Control of [ 13889-98-0 ]

Related Doc. of [ 13889-98-0 ]

Product Details of [ 13889-98-0 ]

Calculated chemistry of [ 13889-98-0 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 13889-98-0 ]

Application In Synthesis of [ 13889-98-0 ]

[ 13889-98-0 ] Synthesis Path-Upstream 1~1

[ 13889-98-0 ] Synthesis Path-Downstream 1~10

Technical Information

Related Functional Groups of [ 13889-98-0 ]

Amides

Related Parent Nucleus of [ 13889-98-0 ]

Aliphatic Heterocycles

Piperazines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

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[ 13889-98-0 ]

Related Parent Nucleus of
[ 13889-98-0 ]