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Method for producing zopiclone

A technology based on zopiclone and pyridyl, which is applied in the field of preparation of zopiclone, can solve problems such as low yield, difficult to guarantee safety, low melting point, etc., and achieve high purity of finished products, short reaction time and high reaction yield Effect

Active Publication Date: 2008-06-11
QILU PHARMA HAINAN +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This method has three problems: 1. flammable materials, safety is difficult to guarantee during large-scale production; 2. The yield is relatively low, the yield of crude product is 76%;
This method has two problems: 1. the yield is relatively low, and the yield of crude product is 81%; Abandonment not only increases the cost, but also is not conducive to environmental protection
3. The melting point is low, which does not meet the requirements of the European Pharmacopoeia

Method used

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  • Method for producing zopiclone
  • Method for producing zopiclone
  • Method for producing zopiclone

Examples

Experimental program
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Effect test

Embodiment 1

[0032] Into a 500ml reaction bottle, 250g of dichloromethane, 10.0g of 6-(5-chloro-2-pyridyl)-5-hydroxyl-7-oxo-5,6-dihydropyrrolo[3,4-b ] pyrazine, 10.0g 1-chloroformyl-4-methylpiperazine hydrochloride, 11ml pyridine, 15ml triethylamine and 1.0g 4-dimethylaminopyridine, warming up to reflux, insulation reaction for 1.5 hours; then , add 100ml of purified water, separate layers, discard the water layer, concentrate dichloromethane in vacuo, add 150ml of ethyl acetate and raise the temperature to 78°C, add 1g of activated carbon, stir for 30 minutes, filter, cool down and crystallize, filter, dry, 13.75 g of zopiclone off-white solid was obtained, with a yield of 92.9% and a content of 98.5% (HPLC).

Embodiment 2

[0034] Into the 500ml reaction bottle, drop 350g methylene chloride, 10.0g 6-(5-chloro-2-pyridyl)-5-hydroxyl-7-oxo-5,6-dihydropyrrolo[3,4-b ] pyrazine, 10.0g 1-chloroformyl-4-methylpiperazine hydrochloride, 11ml pyridine, 15ml diethylamine and 2.0g 4-dimethylaminopyridine, warming up to reflux, insulation reaction for 1 hour; then , add 100ml of purified water, separate layers, discard the water layer, concentrate dichloromethane in vacuo, add 150ml of ethyl acetate and raise the temperature to 78°C, add 1g of activated carbon, stir for 30 minutes, filter, cool down and crystallize, filter, dry, 14.00 g of zopiclone off-white solid was obtained, with a yield of 94.59% and a content of 98.3% (HPLC).

Embodiment 3

[0036] 250g N, N-dimethylformamide, 10.0g 6-(5-chloro-2-pyridyl)-5-hydroxyl-7-oxo-5,6-dihydropyrrolo[ 3,4-b]pyrazine, 10.0g 1-chloroformyl-4-methylpiperazine hydrochloride, 20ml pyridine, 10ml diisopropylamine and 1.0g 4-dimethylaminopyridine, react at 25°C 3.0 hours; then, add 100ml of purified water, separate the layers, discard the water layer, concentrate N,N-dimethylformamide in vacuum, add 150ml of ethyl acetate to raise the temperature to 78°C, add 1g of activated carbon, and stir for 30 minutes. Filter, cool down and crystallize, filter and dry to obtain 13.6 g of zopiclone off-white solid with a yield of 91.89% and a content of 98.0% (HPLC).

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Abstract

A preparation method of zopiclone uses 6-(5-chlorin-2-pyridyl)-5-hydroxy-7-oxo-5, 6-dihydropyrrole [3, 4-b] pyrazine and 1-chlorocarbonyl-4-methylpiperazine hydrochloride as material, in anhydrous organic solvent and alkali condition, uses 4-substituent pyridine as catalyst to prepare the product zopiclone. The inventive method uses the organic solvent with a little toxin and unease burning explosion, via special catalyst to process reaction completely, while the product has high purity and yield.

Description

technical field [0001] The invention relates to a compound synthesis method, in particular to a preparation method of zopiclone. Background technique [0002] Zopiclone, chemical name (5RS)-6-(5-chloro-2-pyridyl)-7-oxo-6,7-dihydro-5H-pyrrolo[3.4-b]pyrazine -5-yl 4-methylpiperazine-1-carboxylate was developed by Rhone-Poulent Rorer, France. Belonging to pyrrocyclone compounds, as a new type of non-benzodiazepine sedative-hypnotics that has been used clinically, it is used for the treatment of insomnia, especially for patients who cannot tolerate the residual effect of the next morning. [0003] As the third generation of non-benzodiazepine hypnotics, it can selectively act on BZI receptors, and the residual effect is relatively small. The phenomenon of "sleeping" in the next morning is rare, and it does not affect the mental activity and movement of the next morning. Sensitivity, and the dose is small, repeated application is also very little accumulation, so it is relative...

Claims

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Application Information

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IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 陈中南魏蒲仁李保勇任保钢
Owner QILU PHARMA HAINAN
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