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Method for preparing phenyl piracetam

A technology of phenylpiracan and benzene, which is used in the field of compound preparation, can solve problems such as low molecular utilization, complex operation, and long response steps to achieve high reaction income and purity, high atomic utilization, response, response, response, response, response, The effect of short steps

Active Publication Date: 2016-11-09
NORTHEAST PHARMA GRP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The method has low molecular utilization, long reaction steps and complex operation, so the process has no market competitive advantage
[0004] In addition, the invention patent with the publication number CN102351726 also introduces a synthetic method similar to the phenylpiracetam intermediate. The method uses p-chlorobenzaldehyde as a raw material, and after addition and ester-forming reaction, it is added with nitromethane , hydrolysis, the nitro group is then reduced to obtain the amino group, and further reduction to the key intermediate 4-phenyl-2-pyrrolidone of phenylpiracetam is required; this method is similar to the above, and there are also low molecular utilization, and the reaction steps Shortcomings of long time and low yield

Method used

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  • Method for preparing phenyl piracetam

Examples

Experimental program
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Effect test

Embodiment 1

[0023] Preparation of ethyl 4-nitro-3-phenylbutyrate

[0024] (1) The influence of different molar ratios of raw materials on the reaction yield:

[0025] Add 200mL of anhydrous methanol, ethyl cinnamate, and nitromethane into the three-necked flask, and slowly add cold 30% NaOH aqueous solution dropwise below 0°C. The selection of different molar ratios of the raw materials is shown in Table 1, 20-30°C React for 24 hours to obtain a reaction solution; concentrate the reaction solution at 40-50°C under reduced pressure to evaporate the organic solvent, add 100ml of water, extract the water phase twice with 80ml of dichloromethane, combine the dichloromethane layers, and wash with 40ml of 1N hydrochloric acid Wash once, and then wash once with 40ml of water to obtain an organic phase extract; add 8g of anhydrous magnesium sulfate to the organic phase extract and dry for 1-2h, filter, and distill off the solvent under reduced pressure to obtain a light yellow oil, namely 4-Nitra...

Embodiment 2

[0037] Preparation of 4-phenyl-2-pyrrolidone

[0038] (1) Adopting the impact of different reduction methods on the reaction yield:

[0039] Dissolve 16.6g (0.07mol) of ethyl 4-nitro-3-phenylbutyrate in 250mL of dichloromethane, stir and cool down to -10°C, slowly add 0.35mol of reducing agent, after the addition is complete, rise to 15-30°C , timed and stirred for 5 hours to obtain the reaction solution. The selection of the reducing agent is shown in Table 1; the reaction solution was cooled to 0°C, 550mL of 10% dilute hydrochloric acid and 550mL of dichloromethane were added, quenched by stirring at 20-30°C, and clarified Extract the aqueous layer with 90mL×2 dichloromethane, combine the dichloromethane layers, and wash three times with 220mL×3 20% aqueous sodium chloride solution; add 8g of anhydrous magnesium sulfate to the organic phase extract and dry for 1-2h , filtered, and dichloromethane was evaporated under reduced pressure to obtain beige solid 4-phenyl-2-pyrroli...

Embodiment 3

[0052] Preparation of 4-phenyl-2-pyrrolidone-1-acetic acid methyl ester

[0053] (1) Adopting the impact of different organic solvents on the reaction yield:

[0054] Dissolve 9.6 g (0.06 mol) of 4-phenyl-2-pyrrolidone in 100 mL of an organic solvent. The selection of the organic solvent is shown in Table 1. Cool down to an internal temperature of -10° C., stir, and add 13.5 g (0.12 mol) Potassium tert-butoxide, after the addition, continue to stir at -10-0°C for 2h, cool down to the internal temperature -10°C, add 13.0g (0.12mol) methyl chloroacetate dropwise, and continue to react at -10-0°C for 2h, After the reaction is complete, add 160mL ethyl acetate, 65mL saturated ammonium chloride / 65mL water, stir and let stand to separate layers, extract the water layer twice with 80mL×2 ethyl acetate, combine the organic layers, wash 2 times with 40mL×2 saturated ammonium chloride Once, washed with 40mL of water once, dried with 8g of anhydrous magnesium sulfate for 30min, filtered...

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Abstract

The invention discloses a method for preparing phenyl piracetam, and belongs to the field of compound preparing. The method includes the following steps that alkali, cinnamic acid alkyl ester and nitromethane are subjected to an addition reaction to obtain 4-nitryl-3-phenylbutyric acid alkyl ester; after nitryl of the 4-nitryl-3-phenylbutyric acid alkyl ester is reduced with a reducing agent, the reduced nitryl and carbonyl are cyclized, and 4-phenyl-2-pyrrolidone is obtained; alkali, haloacetic acid alkyl ester and the 4-phenyl-2-pyrrolidone are subjected to an alkylation reaction to obtain 4-phenyl-2-pyrrolidone-1-acetic acid alkyl ester; the 4-phenyl-2-pyrrolidone-1-acetic acid alkyl ester and ammonia gas are reacted to obtain the phenyl piracetam. The method has the advantages of being short in reaction step, high in atom utilization, more environmentally friendly, safe in operation, high in reaction yield and purity, beneficial for achieving industrialization an the like.

Description

technical field [0001] The invention belongs to the field of compound preparation, in particular to a preparation method of phenylpiracetam. Background technique [0002] Phenylpiracetam, chemical name 4-phenyl-2-pyrrolidone-1-acetamide, is a phenyl derivative of piracetam, first listed in Russia in 1989, for the treatment of cerebrovascular-related diseases, and It has the effect of keeping astronauts awake in space. The drug is clinically used as a drug for the nervous system, with good clinical effects, a wide range of applications, and various therapeutic potentials. [0003] For the synthesis of this compound, there are some related reports. The invention patent "METHOD FORPREPARATION OF GAMMA-AMINO-BETA-PHENYLBUTIRIC ACID HYDROGENCHLORIDE" with publication number LV10710B introduces the synthesis method of phenylpiracetam intermediate, which uses benzaldehyde as raw material and adopts two methods for preparation. One is the key intermediate 4-phenyl-2-pyrrolidone o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/27
CPCC07D207/27
Inventor 沈思思刘九知陶芳王卓张卫军
Owner NORTHEAST PHARMA GRP
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