Preparation method of Oxiracetam

A molar weight and hydroxyl technology, applied in the field of medicinal chemistry, can solve the problems of many reaction steps, complicated operations, and many impurities, and achieve the effects of low cost, simple operation and high product yield.

Inactive Publication Date: 2012-04-04
TIANJIN INSTITUTE OF PHARMA RESEARCH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] In order to overcome many shortcomings in the past, such as many reaction steps, many impurities, repeated separation and purification, cumbersome operation, and high cost, the present invention provides a new method for preparing oxiracetam, which can be obtained by one-step reaction. Product, Oxiracetam

Method used

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  • Preparation method of Oxiracetam
  • Preparation method of Oxiracetam
  • Preparation method of Oxiracetam

Examples

Experimental program
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Effect test

Embodiment 1

[0032] In a 500ml four-neck flask equipped with stirring, thermometer, reflux condenser and drying tube, add 90ml of methanol, slowly add 9.4g of sodium metal in portions, stir and dissolve at room temperature, then add 40.4g (0.4mol) of 4-hydroxyl -2-Pyrrolidone, heated to reflux. Stir and reflux for 1 hour, distill methanol off, add 100ml of dry toluene, continue distilling until the toluene is completely evaporated, and cool to room temperature. Add 100ml of dimethyl sulfoxide, 4.6g, 0.02mol of benzyltriethylammonium chloride (TEBA), drop 41.2g, 0.4mol of 2-chloroacetamide at 30°C, and dissolve it in 200ml In the dimethyl sulfoxide solution, after the dropwise addition was completed, the temperature was raised to 80° C., and the reaction was carried out for 2 hours. After the reaction was completed, filter the filtrate to remove the solvent under reduced pressure, and recrystallize 100 ml of the residue with isopropanol to obtain 18.5 g of white crystals. Tested by YRT-3 ...

Embodiment 2

[0034] In a 500ml four-neck flask equipped with stirring, thermometer, reflux condenser and drying tube, add 90ml of methanol, slowly add 9.4g of sodium metal in portions, stir and dissolve at room temperature, then add 40.4g (0.4mol) of 4-hydroxyl -2-Pyrrolidone, heated to reflux. Stir and reflux for 1 hour, evaporate methanol, add 100ml of dry toluene, continue distillation, wait until the toluene is evaporated, and cool to room temperature. Add 100ml of N,N-dimethylformamide, 4.6g, 0.02mol of benzyltriethylammonium chloride (TEBA), and drop 55.2g, 0.4mol of 2-bromoacetamide at 30°C to make It was dissolved in 200ml of N,N-dimethylformamide solution, and after the dropwise addition was completed, the temperature was raised to 80°C and reacted for 2h. After the reaction was completed, filter the filtrate to remove the solvent under reduced pressure, and recrystallize the residue with 100 ml of isopropanol to obtain 18 g of white crystals. Tested by YRT-3 melting point appar...

Embodiment 3

[0036] In a 500ml four-neck flask equipped with stirring, thermometer, reflux condenser and drying tube, add 90ml of methanol, slowly add 9.4g of sodium metal in portions, stir and dissolve at room temperature, then add 40.4g (0.4mol) of 4-hydroxyl -2-Pyrrolidone, heated to reflux. , stirred and refluxed for 1h, evaporated methanol, added dry toluene (100ml), continued distillation, until the toluene was evaporated, cooled to room temperature. Add 100ml of dry toluene, 6.4g, 0.02mol of tetrabutylammonium bromide (TBAB), and dropwise add 41.2g, 0.4mol of 2-chloroacetamide at 50°C to dissolve it in a solution of 200ml of toluene. After the addition was completed, the temperature was raised to 100° C., and the reaction was carried out for 2 hours. After the reaction was finished, it was filtered, and the filtrate was evaporated to remove the solvent under reduced pressure, and the residue was recrystallized with 100ml of isopropanol to obtain 13g of white crystals. Tested by YR...

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Abstract

The invention provides a method for preparing Oxiracetam, which comprises the following steps: performing alkaline treatment of 4-hydroxy-2-pyrrolidone under a water-free condition; reacting the treated 4-hydroxy-2-pyrrolidone with 2-chloroacetamide in an organic solvent in the presence of a catalyst; and after the reaction is finished, performing filtration, distillation and recrystallization toobtain the Oxiracetam. In the method, the final product can be obtained by a one-step reaction, the operation is simple and convenient, and large scale production can be realized. The invention also provides the Oxiracetam obtained by the method, which has the characteristics of high yield, high purity and good treatment effect. The invention also provides the use of the Oxiracetam obtained by the method in the preparation of medicaments for treating brain dysfunction, impaired memory and senile dementia.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular, the invention relates to a method for preparing oxiracetam, a product obtained by the method and an application of the product. Background technique [0002] Oxiracetam (Oxiracetam), its chemical name is 4-hydroxyl-pyrrolidin-2-one-1-yl acetamide, and its chemical structural formula is as shown in formula (1): [0003] [0004] Formula 1) [0005] The product is used in medicine as a brain function improver. In 1984, it was developed and listed by the Italian ISF company, and it was synthesized for the first time in 1977, see U.S.4118396. [0006] So far, it has been reported that there are many synthetic routes and preparation methods for this product, some of which have many reaction steps, cumbersome operations, and poor purity of intermediates, and some must be purified by chromatographic elution before the next step of reaction can be carried out, which is not suitable...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D207/273A61K31/4015A61P25/28A61P25/00
Inventor 赵世明
Owner TIANJIN INSTITUTE OF PHARMA RESEARCH
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