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Preparation method of levo cloperastine fendizoate

A technology of leverastimine and cloperastine, applied in the field of chemical drug synthesis, can solve the problems of low total yield in the preparation process, and achieve the effects of reducing three waste pollution, simple operation and high safety

Active Publication Date: 2015-02-04
CHONGQING HENG AN CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The levocloperastine fendizaic acid obtained by the method has the advantage of higher optical purity, but the total yield of the preparation process is low

Method used

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  • Preparation method of levo cloperastine fendizoate
  • Preparation method of levo cloperastine fendizoate
  • Preparation method of levo cloperastine fendizoate

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preparation example Construction

[0037] The present invention provides a method for preparing L-cloperastine fendizoic acid, which comprises the following steps:

[0038] Using a resolving agent to resolve racemic cloperastine in a fatty alcohol solvent to obtain L-cloperastine, the resolving agent is L-(-)-diR substituted benzoyl tartaric acid, and the R Is alkyl, alkoxy, -Cl, -F, -Br or -H;

[0039] The L-cloperastine and Fendizic acid are reacted in salt formation to obtain the L-cloperastine Fendizic acid.

[0040] The method provided by the present invention uses L-(-)-diR substituted benzoyltartaric acid as a resolving agent to resolve racemic cloperastine in a fatty alcohol solvent. The resolution yield is high, so that L-cloperastine fendizoic acid has high optical purity and high product yield.

[0041] In addition, the resolving agent and fatty alcohol solvent used in the resolution of racemic cloperastine in the present invention can be repeatedly used, which reduces the cost and reduces the pollution of ...

Embodiment 1

[0113] Into a dry and clean 1000mL three-necked reaction flask, add 300g (1.373mol) 4-chlorobenzyl alcohol, 150g (1.863mol) 2-chloroethanol and 350mL toluene in sequence, stir to dissolve;

[0114] Slowly add 50g of concentrated sulfuric acid dropwise to the solution obtained by dissolving, heating to reflux at a heating rate of 4°C / min, and reacting for 5 hours;

[0115] Cool the obtained reaction product to room temperature, add 100 mL of water to it for extraction, neutralize it with a 42% mass concentration of liquid caustic soda until the pH of the water layer reaches 7, and then separate the water layer;

[0116] The organic layer was distilled under reduced pressure to recover toluene, distilled to an internal temperature of 120° C., and a vacuum of -0.08 MPa or more, to obtain 390 g of oil.

[0117] Put the above-mentioned 390g oily substance into a 2000mL dry and clean three-necked reaction flask, add 150g anhydrous sodium carbonate and 180g (2.118mol) piperidine to it, and he...

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Abstract

The invention discloses a preparation method of levo cloperastine fendizoate, which comprises the following steps: carrying out nucleophilic substitution reaction on 4-chlorobenzhydrol and 2-chloroethanol in a benzene organic solvent, so that an intermediate product is obtained; reacting the intermediate product with piperidine, so that racemic cloperastine is obtained; resolving the racemic cloperastine by using a resolving agent in a fatty alcohol solvent, so that levo cloperastine is obtained; and carrying out salt forming reaction on the levo cloperastine and a fendizoic acid, so that levo cloperastine fendizoate is obtained, wherein the resolving agent is an R-substituted dibenzoyl-L-tartaric acid, and R refers to alkyl, alkoxy, -Cl, -F, -Br or -H. In the method provided by the invention, in a fatty alcohol solvent, an R-substituted dibenzoyl-L-tartaric acid is adopted as a resolving agent for carrying out resolving on racemic cloperastine, and the resolving yield is high, so that the obtained levo cloperastine fendizoate has high optical purity, and has a high product yield.

Description

Technical field [0001] The present invention relates to the technical field of chemical drug synthesis, in particular to a method for preparing L-cloperastine fenditaric acid. Background technique [0002] Racemic cloperastine itself has good biological activity and drug activity. It is a central antitussive. It mainly inhibits the cough center and suppresses cough. It also has a weak antihistamine effect. It has no addiction and tolerance. Clinically used for cough caused by upper respiratory tract infection. However, L-cloperastine fenditosic acid has higher clinical drug activity, and its curative effect is multiple times that of racemic cloperastine. It has basically no side effects and can be used as a medicine for children. Therefore, this product has a large market demand. , The prospects are good. [0003] At present, the known preparation methods of L-cloperastine fenditosic acid mainly include: for example, racemic 4-chlorobenzyl alcohol is used as the starting material...

Claims

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Application Information

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IPC IPC(8): C07D295/088
CPCC07D295/088
Inventor 陶文潘潘文驰潘兴长罗泳萍樊希祥
Owner CHONGQING HENG AN CHEM CO LTD
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