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ChemicalBook >> CAS DataBase List >>1-Benzyl-4-piperidone

1-Benzyl-4-piperidone

CAS No.
3612-20-2
Chemical Name:
1-Benzyl-4-piperidone
Synonyms
1-BENZYLPIPERIDIN-4-ONE;1-BENZYL-4-PIPERIDONE;Benzyl piperidone;N-Benzylpiperidin-4-one;NSC 77933;-4-piperidone;N-BENZYLPIPERIDONE;1-Benzylpiperidone;BENZYLPIPERIDONE-4;Benzamide,7-bromo-
CBNumber:
CB8341198
Molecular Formula:
C12H15NO
Molecular Weight:
189.25
MDL Number:
MFCD00006192
MOL File:
3612-20-2.mol
MSDS File:
SDS
Last updated:2024-09-18 10:41:30

1-Benzyl-4-piperidone Properties

Boiling point 134 °C7 mm Hg(lit.)
Density 1.021 g/mL at 25 °C(lit.)
vapor pressure 0.079-0.15Pa at 20-25℃
refractive index n20/D 1.541(lit.)
Flash point >230 °F
storage temp. 2-8°C
solubility 12g/l
form Oily Liquid
pka 7.07±0.20(Predicted)
Specific Gravity 1.021
color Clear colorless to straw
Water Solubility 12 g/L (20 ºC)
BRN 128556
LogP 2.1 at 20℃ and pH9
CAS DataBase Reference 3612-20-2(CAS DataBase Reference)
FDA UNII 399249PH5B
NIST Chemistry Reference 4-Piperidinone, 1-(phenylmethyl)-(3612-20-2)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H302-H315-H319
Precautionary statements  P264-P270-P280-P301+P312-P302+P352-P305+P351+P338
Hazard Codes  Xi,Xn
Risk Statements  36/37/38-43-22-20/21/22
Safety Statements  26-36-37/39
WGK Germany  3
Hazard Note  Irritant
HS Code  29333999
NFPA 704
2
2 0

1-Benzyl-4-piperidone price More Price(46)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich B29806 1-Benzyl-4-piperidone 99% 3612-20-2 25g $41.6 2024-03-01 Buy
Sigma-Aldrich B29806 1-Benzyl-4-piperidone 99% 3612-20-2 100g $80.1 2024-03-01 Buy
TCI Chemical B1027 1-Benzyl-4-piperidone >98.0%(GC)(T) 3612-20-2 25mL $30 2024-03-01 Buy
TCI Chemical B1027 1-Benzyl-4-piperidone >98.0%(GC)(T) 3612-20-2 500mL $282 2024-03-01 Buy
Alfa Aesar A12390 1-Benzyl-4-piperidone, 98+% 3612-20-2 25g $28.65 2024-03-01 Buy
Product number Packaging Price Buy
B29806 25g $41.6 Buy
B29806 100g $80.1 Buy
B1027 25mL $30 Buy
B1027 500mL $282 Buy
A12390 25g $28.65 Buy

1-Benzyl-4-piperidone Chemical Properties,Uses,Production

Chemical Properties

Clear colorless to straw coloured oily liquid

Uses

1-Benzyl-4-piperidone is a pharmaceutical intermediate, it is used in penfluridol synthesis of bulk drugs.

Uses

A substituted piperidine as pesticide

Reactions

As an important organic compound, N-Benzyl-4-piperidone could be used to synthesize many organic compounds. There are four ways to synthesize 1-benzylpiperidine-4-carbaldehyde using it as the raw material. The first method involves the Wittig reaction of (methoxymethyl) triphenylphosphonium chloride with N-benzyl-4-piperidone, followed by hydrolysis of the resulting enol ether. In another method, trimethylsilyl diazomethane is condensed with N-benzyl-4-piperidone, followed by hydrolysis to obtain the final product. In a third route, N-benzyl-4-piperidone is treated with trimethyloxosulfonium iodide to produce the corresponding epoxide. The epoxide is then rearranged in the presence of magnesium bromide etherate, resulting in 1-benzylpiperidine-4-carbaldehyde with high yields. In 2007, a patent described the Darzens condensation of N-benzyl-4-piperidone with ethyl chloroacetate, followed by decarboxylation[1].
N-Benzyl-4-piperidone

Synthesis

1-Benzyl-4-piperidone was synthesized with benzylamine and methyl acrylate as raw materials via 1,4-addition, Dieckmann condensation and hydrolysis decarboxylafion reactions. Add 150 mL of anhydrous toluene and 2.8 g of metallic sodium to a 250 mL dry three-necked flask, stir and heat to reflux. Add 1 mL of anhydrous methanol, then slowly drop 28 g of N.N-bis(β-propionate methyl ester) benzylamine. After adding N.N-bis(β-propionate methyl ester), benzylamine is completed, reflux for 6 h. During the reflux process, the stirring speed needs to be increased, and 100 ml of anhydrous toluene is added to the reaction vessel in batches. Stop reflux, cool to room temperature, extract the mixture with 150 mL of 25% (mass fraction) hydrochloric acid solution, and reflux in an oil bath for 5 h until there is no colour change in the FeCl3 solution test, indicating that the reaction is over. Cool the reaction mixture, add 35% NaOH solution while stirring to neutralize to about pH=8.5, extract with ethyl acetate (100 ml×3), combine the ethyl acetate layers, wash with saturated NaCl solution, and dry over anhydrous magnesium sulfate. Ethyl acetate was recovered by distillation, and the remaining material was distilled under reduced pressure to obtain 14.8 g of 1-benzyl-4-piperidone with a yield of 78.4%. The product was a light yellow oily liquid.

Purification Methods

If the physical properties show contamination, then dissolve it in the minimum volume of H2O, made strongly alkaline with aqueous KOH, extract it with toluene several times, dry the extract with K2CO3, filter, evaporate and distil the residue at high vacuum using a bath temperature of 160-190o, and redistil it. [Brookes & Walker J Chem Soc 3173 1957, Bolyard J Am Chem Soc 52 1030 1930.] The hydrochloride has m 159-161o (from Me2CO/Et2O), and the picrate has m 174-182o (from Me2CO/Et2O). [Grob & Brenneisen Helv Chim Acta 41 1184 1958, Beilstein 21/6 V 424.]

References

[1] Chavakula R, et al. Industrially Viable Preparation ofN-Benzyl-4-formylpiperidine, a Key Intermediate of Donepezil. Organic Preparations and Procedures International, 2013; 45: 168-170.

41979-39-9
100-39-0
3612-20-2
Synthesis of 1-Benzyl-4-piperidone from 4-oxopiperidinium chloride and Benzyl bromide
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Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
1-Benzyl-4-piperidone pictures 2024-12-12 1-Benzyl-4-piperidone
3612-20-2
 US $60.00 / kg 1kg 99.9% 2000kg hebei hongtan Biotechnology Co., Ltd
N-Benzyl-4-piperidone pictures 2024-12-11 N-Benzyl-4-piperidone
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 US $10.00 / kg 1kg 99.9% 10000 Hebei Miaoyin Technology Co.,Ltd
N-Benzyl-4-piperidone pictures 2024-11-11 N-Benzyl-4-piperidone
3612-20-2
 US $10.00-7.00 / kg 1kg 99.99% 10 tons Shandong Deshang Chemical Co., Ltd.
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