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Preparation method of rupatadine fumarate intermediate 5-methyl-3-chloromethylpyridine hydrochloride

A technology of chloromethylpyridine hydrochloride and rupatadine fumarate, applied in the field of synthesis of rupatadine fumarate, can solve the problems of poor product purity, difficult purification, harsh production conditions, etc. It achieves the effects of convenient post-treatment purification, improved product purity, and convenient operation

Inactive Publication Date: 2021-07-16
BEIJING JIALIN PHARM INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] The preparation of 5-methyl-3-chloromethylpyridine hydrochloride as an important intermediate has problems such as difficult purification or harsh conditions
The synthesis of this intermediate belongs to the chlorination reaction. It is reported in the existing literature that a large amount of thionyl chloride is used as the reaction reagent and solvent for similar reactions. After the reaction, the thionyl chloride is directly distilled out. The thionyl chloride, the product purity is also poor
[0008] Thionyl chloride, SOCl 2 It is a fuming liquid with a strong pungent smell. When it meets water, it will exotherm violently and release a large amount of corrosive hydrochloric acid gas and sulfurous acid, which will have a strong irritating effect on human eyes, mucous membranes, skin and upper respiratory tract. After inhalation, It may be fatal due to throat, bronchospasm, inflammation and edema. The industrial production conditions of a large amount of thionyl chloride are extremely harsh, which is very harmful to humans and the environment.

Method used

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  • Preparation method of rupatadine fumarate intermediate 5-methyl-3-chloromethylpyridine hydrochloride
  • Preparation method of rupatadine fumarate intermediate 5-methyl-3-chloromethylpyridine hydrochloride
  • Preparation method of rupatadine fumarate intermediate 5-methyl-3-chloromethylpyridine hydrochloride

Examples

Experimental program
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Effect test

Embodiment 1

[0030] Add 49.8g of 5-methyl-3-hydroxymethylpyridine and 300g of dioxane into a 1000mL single-necked flask, add 57.7g of thionyl chloride dropwise at room temperature, and after the dropping, raise the temperature to 110°C and reflux for 2 hours. Concentrate under reduced pressure to remove 40%-50% of the solvent content of the reaction solution, add 100mL n-heptane to the residue, stir and disperse, cool to room temperature for rapid crystallization, filter to collect the precipitate, rinse the filter cake with 20mL n-heptane, and place it in an oven at 60°C dry. A khaki solid particle weighing 64.4 g was obtained, with a yield of 90% and a purity of 99.6%.

Embodiment 2

[0032] Add 100g of 5-methyl-3-hydroxymethylpyridine and 500g of dioxane into a 1000mL one-necked flask, add 100.8g of thionyl chloride dropwise at room temperature, and after the dropping, raise the temperature to 110°C and reflux for 2 hours. Concentrate under reduced pressure to remove 40%-50% of the solvent content of the reaction solution, add 200mL n-heptane to the residue, stir and disperse, cool to room temperature for rapid crystallization, filter to collect the precipitate, rinse the filter cake with 40mL n-heptane, and place it in an oven at 60°C dry. A khaki solid particle was obtained, weighing 132.4 g, with a yield of 92% and a purity of 99.3%.

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Abstract

The present invention relates to a preparation method for a rupatadine fumarate intermediate, namely 5-methyl-3-chloromethylpyridine hydrochloride. The preparation method comprises the following steps: 1, carrying out a reaction on a 5-methyl-3-hydroxymethylpyridine solution and thionyl chloride to generate 5-methyl-3-chloromethylpyridine hydrochloride; and 2, carrying out reduced-pressure concentration to remove a part of a solvent in reaction liquid, adding an organic solvent for rapid crystallization, and conducting stirring and filtering to obtain the 5-methyl-3-chloromethylpyridine hydrochloride.

Description

Technical field: [0001] The invention relates to a purification method of a pharmaceutical intermediate compound, in particular to a rapid crystallization purification method of rupatadine fumarate intermediate 5-methyl-3-chloromethylpyridine hydrochloride and its purification method in rich Application in the synthesis of rupatadine maleate. Background technique: [0002] Rupatadine fumarate has the following structural formula: [0003] [0004] As a dual antagonist of histamine and platelet aggregation, rupatadine fumarate is mainly used in the treatment of allergic diseases such as allergic rhinitis and urticaria. [0005] It is known that 5-methyl-3-chloromethylpyridine hydrochloride is an important intermediate for the preparation of rupatadine fumarate. [0006] [0007] The preparation of 5-methyl-3-chloromethylpyridine hydrochloride as an important intermediate has problems such as difficult purification or harsh conditions. The synthesis of this intermedia...

Claims

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Application Information

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IPC IPC(8): C07D213/26
CPCC07D213/26
Inventor 徐贵远
Owner BEIJING JIALIN PHARM INC
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