2-(4- OBzl-2-oxo-2,5-pyrroline-1-yl)-acetamide and synthesis and application thereof

A technology of dihydropyrrole and benzyloxy, which is applied in the application field of key intermediates, can solve the problems that purification cannot meet industrial production requirements, complicated operation, low total yield, etc., and achieves good industrial application prospects and cheap and easy raw materials. The effect of high yield and product yield

Inactive Publication Date: 2012-07-04
HANGZHOU NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The earliest synthetic method is to synthesize pyrrolidine first, and then obtain the target product through steps such as reduction, substitution, and ammoniation. The main problems are that there are many reaction steps, long time consumption, low overall yield, and low atom economy. In addition, raw materials are not easy to obtain and expensive, intermediates or products are not easy to purify, and some processes even use highly toxic substances;
[0008] To sum up, the main disadvantages of the current synthetic routes are that the raw materials are expensive and difficult to obtain, some of them are highly toxic, low in safety, the synthetic route is long, the operation is complicated, the purification cannot meet the requirements of industrial production, and the environmental pollution is serious

Method used

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  • 2-(4- OBzl-2-oxo-2,5-pyrroline-1-yl)-acetamide and synthesis and application thereof
  • 2-(4- OBzl-2-oxo-2,5-pyrroline-1-yl)-acetamide and synthesis and application thereof
  • 2-(4- OBzl-2-oxo-2,5-pyrroline-1-yl)-acetamide and synthesis and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Example 1 Synthesis of 3-benzyloxy-4-chloro-2-butenoic acid methyl ester.

[0038] Method 1: Take a dry 100mL three-neck round bottom flask, add 1.5g (0.01mol) methyl 4-chloroacetoacetate, 1.08g (0.01mol) benzyl alcohol and 45mg p-toluenesulfonic acid, add 30mL Cyclohexane, magnetic stirring, oil bath heating, water separator reflux, reaction for 5h, cooling to room temperature, desolvation under reduced pressure, to obtain a light yellow oily liquid, which is 3-benzyloxy-4-chloro-2-butene Acid methyl ester, gas phase yield 15.20%, directly used in next step reaction.

[0039] Method 2: Take a dry 100mL three-neck round bottom flask, add 1.5g (0.01mol) methyl 4-chloroacetoacetate, 1.08g (0.01mol) benzyl alcohol and 5mL aluminum chloride solution, add 30mL Cyclohexane, magnetic stirring, oil bath heating, water separator reflux, reaction for 5h, cooling to room temperature, desolvation under reduced pressure, to obtain a light yellow oily liquid, which is 3-benzyloxy-4-...

Embodiment 2

[0043] Example 2 Synthesis of 2-(4-benzyloxy-2-oxo-2,5-dihydropyrrol-1-yl)-acetamide 2.

[0044] Method 1. 2.40g (about 0.01mol) of 3-benzyloxy-4-chloro-2-butenoic acid methyl ester prepared in Example 1, 1.12g (0.01mol) glycinamide hydrochloride and 30mL methanol Put the solvent in a 100mL three-necked flask, add 10mol / L sodium carbonate solution dropwise under stirring, keep the pH of the system between 8-9, stir magnetically for 14 hours at a temperature of 60°C, then add 15mL of distilled water, stir and filter with suction , a yellow viscous crude product was obtained. The crude product was recrystallized several times with a recrystallization solvent to obtain a yellow powdery solid, GC-MS: m / z=246[M] + And there is only one peak, the yield is 70.26%. Melting point: 247.2-248.6°C.

[0045] Method 2. 2.40g (about 0.01mol) of 3-benzyloxy-4-chloro-2-butenoic acid methyl ester prepared in Example 1, 1.12g (0.01mol) glycinamide hydrochloride and 30mL methanol Put the solv...

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Abstract

The invention discloses 2-(4- OBzl-2-oxo-2,5-pyrroline-1-yl)-acetamide and synthesis and application thereof. The structure of 2-(4- OBzl-2-oxo-2,5-pyrroline-1-yl)-acetamide is indicated as the formula (3), and the synthesis route is indicated as follows. 2-(4- OBzl-2-oxo-2,5-pyrroline-1-yl)-acetamide can serve as an intermediate to be used for synthesis of oxiracetam, has the advantages that synthesis steps are short, operation is simple and convenient, raw materials are cheap and easy to obtain and emission of three wastes is little, and enjoys broad industrial application prospects.

Description

(1) Technical field [0001] The present invention relates to 2-(4-benzyloxy-2-oxo-2,5-dihydropyrrol-1-yl)-acetamide, its synthesis method and its use as a synthetic pyrrolidone nootropic drug oxiracetam Application of key intermediates. (2) Background technology [0002] Oxiracetam, whose chemical name is 4-hydroxy-2-oxo-1-pyrrolidineacetamide, has the following structure: [0003] [0004] Oxiracetam is a pyrrolidone nootropic drug, which is clinically used to treat brain insufficiency caused by various reasons. It is currently considered to be one of the most promising new nootropic drugs. The drug can act on the hippocampus, cerebral cortex and striatum with high selectivity, and has the effects of enhancing memory and anti-amnesia. [0005] Oxiracetam was first developed and synthesized by the Italian ISF company in 1974, and it went on the market in 1987. So far, many companies have applied for patents on the synthesis process of oxiracetam, and there are mainly tw...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/273
Inventor 郑辉刘娟施巧月梅怡嘉章鹏飞
Owner HANGZHOU NORMAL UNIVERSITY
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