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Method for preparing cyclopentyl phenyl acetaldehyde

A technology of cyclopentylphenyl and cyclopentylphenyl oxirane, which is applied in the field of preparation of cyclopentylphenylacetaldehyde, can solve problems affecting the quality of penhyclidine hydrochloride, etc., and achieve easy operation and improved The effect of quality standards and easy-to-obtain raw materials

Inactive Publication Date: 2019-10-18
WUHAN DOCAN PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Combined with the analysis of the production process of penhyclidine hydrochloride, it is likely that cyclopentylphenylacetaldehyde impurities will be produced, which will affect the quality of penhyclidine hydrochloride

Method used

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  • Method for preparing cyclopentyl phenyl acetaldehyde
  • Method for preparing cyclopentyl phenyl acetaldehyde
  • Method for preparing cyclopentyl phenyl acetaldehyde

Examples

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Effect test

Embodiment 1

[0038] A preparation method of cyclopentylphenylacetaldehyde, comprising the following steps:

[0039] (1) Weigh 20 g of cyclopentylphenyl oxirane, add it to the reaction flask, add 200 g of tetrahydrofuran, stir and dissolve, then add 16.7 g of indium trichloride;

[0040] (2) Stir, react at 25-30°C for 3 hours, add 200g of water after the reaction to quench the reaction, add ethyl acetate for extraction, 100g each time, combine the organic phases and add 50g of anhydrous sodium sulfate to dry for 1 hour, after drying, filter Sodium sulfate was removed and concentrated to obtain 12.4 g of an oily substance.

[0041] (3) Add 20 g of ethyl acetate to dissolve the obtained oil, add 25 g of silica gel, stir evenly, concentrate to dryness, and set aside. Weigh 300g of silica gel, add hexane and stir evenly, pour it into a glass column for sedimentation, after the column is packed, add silica gel with sample, then add a mixed solution of hexane and ethyl acetate to elute, the hexa...

Embodiment 2

[0050] A preparation method of cyclopentylphenylacetaldehyde, comprising the following steps:

[0051] (1) Weigh 25 g of cyclopentylphenyl oxirane, add it into a reaction flask, add 300 g of tetrahydrofuran, stir to dissolve, and then add 18.5 g of indium trichloride.

[0052] (2) Stir, react at 20-25°C for 4 hours, add 250g of water after the reaction to quench the reaction, then extract with ethyl acetate, 125g each time, combine the organic phases and add 50g of anhydrous sodium sulfate to dry for 2 hours, after drying, filter Sodium sulfate was removed and concentrated to obtain 16.3 g of oily substance.

[0053] (3) Add 30 g of ethyl acetate to dissolve the obtained oil, add 32 g of silica gel, stir evenly, concentrate to dryness, and set aside. Weigh 350g of silica gel, add hexane and stir evenly, pour it into a glass column to settle, after the column is packed, add silica gel with sample, then add a mixed solution of hexane and ethyl acetate for elution, the hexane an...

Embodiment 3

[0055] A preparation method of cyclopentylphenylacetaldehyde, comprising the following steps:

[0056] (1) Weigh 10 g of cyclopentylphenyl oxirane, add it into a reaction flask, add 100 g of tetrahydrofuran, stir to dissolve, and then add 7.1 g of indium trichloride.

[0057] (2) Stir, react at 25-30°C for 4 hours, add 100g of water after the reaction to quench the reaction, then extract with ethyl acetate, 50g each time, combine the organic phases and add 30g of anhydrous sodium sulfate to dry for 1 hour, after drying, filter Sodium sulfate was removed and concentrated to obtain 5.9 g of oil.

[0058] (3) Add 10 g of ethyl acetate to dissolve the obtained oil, add 12 g of silica gel, stir evenly, concentrate to dryness, and set aside. Weigh 120g of silica gel, add hexane and stir evenly, pour into a glass column for sedimentation, after the column is packed, add silica gel with sample, then add a mixed solution of hexane and ethyl acetate for elution, the hexane and ethyl ac...

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Abstract

The invention discloses a method for preparing cyclopentyl phenyl acetaldehyde. The method comprises the following steps: by taking cyclopentyl phenyl ethylene oxide as a raw material, lewis acid as acatalyst, performing a reaction so as to obtain cyclopentyl phenyl acetaldehyde, specifically, dissolving cyclopentyl phenyl ethylene oxide into an organic solvent, adding lewis acid as the catalyst,performing a stirring reaction, adding water to implement a quenching reaction, further adding an extraction agent for extraction, collecting an organic phase, further adding a drying agent, performing filtration and concentration so as to obtain an oily substance, and performing column chromatography isolation on the obtained oily substance so as to obtain the cyclopentyl phenyl acetaldehyde. Byadopting the method disclosed by the invention, a reference product for qualitative and quantitative analysis can be provided for detection on penehyclidine hydrochloride, and the quality standard ofthe penehyclidine hydrochloride can be improved; the impurity cyclopentyl phenyl acetaldehyde is simple and convenient to prepare, the used raw materials are easy to obtain, and the impurity is low in preparation cost, high in purity and controllable in quality.

Description

technical field [0001] The invention relates to the technical field of pharmacy, in particular to a preparation method of cyclopentylphenylacetaldehyde. Background technique [0002] Penehyclidine hydrochloride is a kind of potent anticholinergic drug independently developed by my country, and its chemical name is 3-(2-cyclopentyl-2-hydroxyl-2-phenylethoxy)quinuclidine hydrochloride. In the acute treatment of organophosphate poisoning (pesticide) poisoning and in the later stage of poisoning or after the aging of cholinesterase (ChE), atropineization is maintained (atropineization refers to the use of a certain dose of atropine in patients with organophosphorus poisoning to limit the body to the maximum physiological tolerance of atropine). Borderline state between limit and atropine poisoning). Its chemical structural formula is as follows: [0003] [0004] The chemical structure of penehyclidine hydrochloride is a tertiary amine salt, which can enter the brain through ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/58C07C47/235
CPCC07C45/58C07C2601/08C07C47/235
Inventor 黄岭朱墨吴俊李全军胡金涛
Owner WUHAN DOCAN PHARMA
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