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Oxiracetam compound and new method thereof

A compound and new method technology, applied in the field of medicine, can solve the problems of complex preparation process, high cost, cumbersome steps, etc.

Active Publication Date: 2010-12-15
HAINAN LINGKANG PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0017] The purpose of the present invention is to provide a new method for synthesizing oxiracetam compounds, which solves the disadvantages of complex preparation process, cumbersome steps, high cost, low product purity and difficult purification in the prior art

Method used

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  • Oxiracetam compound and new method thereof
  • Oxiracetam compound and new method thereof
  • Oxiracetam compound and new method thereof

Examples

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Effect test

Embodiment 1

[0036] The synthesis of embodiment 1 4-chloro-3-hydroxyl-butanamide

[0037] Add 478g (4mol) 3-chloro-2-hydroxypropionitrile and 500ml concentrated sulfuric acid into a three-necked reaction flask, stir, heat up to 50°C, react for 2h, then cool to room temperature, and pour the reactant into 2000ml of ice-water mixture , stirred, extracted three times with 800ml of ethyl acetate respectively, the organic phase was dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 495g of oil product, with a yield of 90%.

Embodiment 2

[0038] The synthesis of embodiment 2 4-hydroxyl-2-pyrrolidone

[0039] Mix 275g (2mol) 4-chloro-3-hydroxy-butyramide, 2L of absolute ethanol, and 85g of sodium hydroxide, the intermediate of the previous step, raise the temperature to 50°C, react for 15h, then distill under reduced pressure to recover ethanol, and in the residue Add 1000 ml of ethyl acetate, stir for 30 min, filter to remove insoluble matter, concentrate ethyl acetate under reduced pressure, and recrystallize the residue with isopropanol to obtain 161 g of white solid 4-hydroxy-2-pyrrolidone with a yield of 80%.

Embodiment 3

[0040] Example 3 Synthesis of 4-hydroxyl-2-pyrrolidone ethyl acetate

[0041] Add 1000ml of isopropyl ether, 101g (1mol) of 4-hydroxy-2-pyrrolidone, 60g of sodium methoxide into the reaction flask, stir and heat to reflux, stir for 5h, the solution becomes a clear liquid, then slowly add 122g (1mol) The solution formed by ethyl chloroacetate and 500ml isopropyl ether, while keeping the reaction in the reflux state, continued to react for 5h after the dropwise addition, then cooled to room temperature, filtered to remove the solid residue in the reaction solution, recovered the solvent under reduced pressure, and then decompressed The product was distilled to obtain 147g of colorless liquid with a yield of 79%.

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Abstract

The invention relates to an oxiracetam compound and a new method thereof. In the method, 3-chloro-2-hydroxy propionitrile is used as an initial raw material. The method comprises the following steps of: synthesizing 4-hydroxyl-2-pyrrolidone through 4-chloro-3-hydroxyl-butylamide; and then synthesizing oxiracetam. The invention overcomes the defects of complicated preparation process, trouble steps, high cost, low product purity and difficult purification of the prior art.

Description

technical field [0001] The invention relates to an oxiracetam compound and a new method thereof, belonging to the technical field of medicine. Background technique [0002] Oxiracetam, chemical name: 4-hydroxy-2-oxo-1-pyrrolidineacetamide, molecular formula: C 6 h 10 N 2 o 3 Molecular weight: 158.16, structural formula: [0003] [0004] Oxiracetam is an analogue of piracetam, which can improve memory and learning functions in patients with Alzheimer's disease and memory impairment. Mechanistic research results suggest that oxiracetam can promote the synthesis of phosphorylcholine and phosphorylethanolamine, increase the ratio of ATP / ADP in the brain, and increase the synthesis of protein and nucleic acid in the brain. [0005] Oxiracetam was synthesized for the first time in 1974 by the Italian Shikebichem Company and launched in 1984. It is a consumer product composed of two isomers (S)-Oxiracetam and (R)-Oxiracetam. Spin body. At present, there are multiple synt...

Claims

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Application Information

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IPC IPC(8): C07D207/273
Inventor 胡建荣
Owner HAINAN LINGKANG PHARMA CO LTD
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