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Synthesis method of rupatadine intermediate namely 3-chloromethyl-5-methylpyridine

A technology of picoline and synthetic method, applied in the direction of organic chemistry, can solve the problem that intermediates cannot be mass-produced at low cost, and achieve the effect of low cost and good application prospect

Inactive Publication Date: 2016-04-20
江苏笃诚医药科技股份有限公司
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Problems solved by technology

[0003] Synthesis using 3-chloromethyl-5-picoline as a raw material has good prospects in the currently known and feasible rupatadine production process, but is limited by the fact that the intermediate cannot be mass-produced at an appropriate cost

Method used

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Embodiment Construction

[0015] The present invention will be described in more detail through preferred embodiments below.

[0016] The synthetic method of rupatadine intermediate 3-chloromethyl-5-picoline, comprises the steps:

[0017] (3) Put 3,5-lutidine and concentrated sulfuric acid into the reaction kettle with ultraviolet light,

[0018] (4) Feed chlorine into the reactor in step (1), and react under ultraviolet light for 12 to 24 hours,

[0019] (3) Add water to the solution in the reactor after step (2) until the pH of the solution is adjusted to weak alkaline,

[0020] (4) Extract the solution obtained in step (3) with toluene, then pass hydrogen chloride gas into the toluene layer to precipitate the product, and obtain pure 3-chloromethyl-5-picoline hydrochloride after recrystallization of the obtained product .

[0021] The recrystallization described in step (4) uses a mixture of isopropanol and water as a solvent.

[0022] The concentrated sulfuric acid in step (1) is oleum with a m...

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Abstract

The invention discloses a synthesis method of a rupatadine intermediate namely 3-chloromethyl-5-methylpyridine. The method comprises the following steps: (1) adding 3,5-dimethylpyridine and concentrated sulfuric acid into a reactor with UV radiation; (2) introducing chlorine gas into the reactor in the step (1), and carrying out reactions for 12 to 24 hours under the irradiation of UV light; (3) adding water into the solution obtained in the step (2) after reactions until the pH value of the solution falls in the weak alkaline area; (4) extracting the solution obtained in the step (3) by toluene, then introducing hydrogen chloride gas into the toluene layer to precipitate the product, and re-crystallizing the obtained product to obtain a pure product of 3-chloromethyl-5-methylpyridine hydrochloride. The provided method can industrially obtain 3-chloromethyl-5-methylpyridine in a low cost.

Description

technical field [0001] The invention relates to a synthesis method of rupatadine intermediate 3-chloromethyl-5-picoline. Background technique [0002] The chemical name of rupatadine is 8-chloro-6,11-dihydro-11-[1-[(5-methyl-3-pyridyl)methyl]-4-piperidinylidene]- 5H-Benzo[5,6]cyclohepta[1,2-b]pyridine. The drug was developed by Uriach Company of Spain and first launched in Spain in March 2003. The approved indications are seasonal allergic rhinitis (SAR) and perennial allergic rhinitis (PAR). [0003] Synthesis using 3-chloromethyl-5-picoline as a raw material has good prospects in the currently known and feasible rupatadine production process, but is limited by the fact that the intermediate cannot be mass-produced at an appropriate cost. Contents of the invention [0004] Aiming at the deficiencies in the prior art, the object of the present invention is to provide a method for the industrial production of 3-chloromethyl-5-picoline at low cost. [0005] To achieve the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/26
Inventor 王笃政王玉祥王川民李民权
Owner 江苏笃诚医药科技股份有限公司
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