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

1-Benzyl-4-piperidone

Product Name
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
Formula Weight
189.25
MOL File
3612-20-2.mol
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1-Benzyl-4-piperidone Property

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)
NIST Chemistry Reference
4-Piperidinone, 1-(phenylmethyl)-(3612-20-2)
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Safety

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
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
B29806
Product name
1-Benzyl-4-piperidone
Purity
99%
Packaging
25g
Price
$41.6
Updated
2024/03/01
Sigma-Aldrich
Product number
B29806
Product name
1-Benzyl-4-piperidone
Purity
99%
Packaging
100g
Price
$80.1
Updated
2024/03/01
TCI Chemical
Product number
B1027
Product name
1-Benzyl-4-piperidone
Purity
>98.0%(GC)(T)
Packaging
25mL
Price
$30
Updated
2024/03/01
TCI Chemical
Product number
B1027
Product name
1-Benzyl-4-piperidone
Purity
>98.0%(GC)(T)
Packaging
500mL
Price
$282
Updated
2024/03/01
Alfa Aesar
Product number
A12390
Product name
1-Benzyl-4-piperidone, 98+%
Packaging
25g
Price
$28.65
Updated
2024/03/01
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1-Benzyl-4-piperidone Chemical Properties,Usage,Production

Chemical Properties

Clear colorless to straw coloured oily liquid

Uses

A substituted piperidine as pesticide

Uses

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

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].

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.

1-Benzyl-4-piperidone Preparation Products And Raw materials

Raw materials

Benzylamine Methyl propionate 4,4-Piperidinediol hydrochloride

Preparation Products

N-Boc-2-piperidone 4,5,6,7-TETRAHYDRO-2-METHYLFURO[3,2-C]PYRIDINE 1-BOC-4-HYDROXY-4-(HYDROXYMETHYL)-PIPERIDINE 4-(3-Trifuoromethyl)phenyl-4-piperidinol 1-BENZYL-4-HYDROXY-4-(3-TRIFLUOROTOLYL)PIPERIDINOL 1H-Azepine-4-carboxylicacid,hexahydro-,methylester,(4S)-(9CI) 4-(1-Pyrrolidinyl)piperidine 1H-Azepine-4-carboxylicacid,hexahydro-,methylester,(4R)-(9CI)
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View Lastest Price from 1-Benzyl-4-piperidone manufacturers

hebei hongtan Biotechnology Co., Ltd
Product
1-Benzyl-4-piperidone 3612-20-2
Price
US $60.00/kg
Min. Order
1kg
Purity
99.9%
Supply Ability
2000kg
Release date
2024-05-16
Hebei Miaoyin Technology Co.,Ltd
Product
N-Benzyl-4-piperidone 3612-20-2
Price
US $10.00/kg
Min. Order
1kg
Purity
99.9%
Supply Ability
10000
Release date
2023-04-06
Shandong Deshang Chemical Co., Ltd.
Product
N-Benzyl-4-piperidone 3612-20-2
Price
US $10.00-7.00/kg
Min. Order
1kg
Purity
99.99%
Supply Ability
10 tons
Release date
2024-06-06

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