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Method for preparing tropisetron hydrochloride on large scale

A technology of tropisetron hydrochloride and tropisetron, which is applied in the direction of organic chemistry, can solve the problems of high price, and achieve the effects of simple operation, cost saving and increased safety

Inactive Publication Date: 2012-07-18
湖南康普医药研究院
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Problems solved by technology

[0005] In the literature [Synthetic Improvement of Tropisetron Hydrochloride, Journal of Huaihai Institute of Technology, 2003; 12 (4): 41~43; Improvement of Synthetic Process of Tropisetron Hydrochloride, Journal of Hunan Normal University (Medical Edition), 2006; 3 (4): 29~30], tropisetron hydrochloride was obtained in yields of 50% and 52.8%, respectively, but expensive n-butyllithium was still used as the activator of the condensation reaction

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  • Method for preparing tropisetron hydrochloride on large scale
  • Method for preparing tropisetron hydrochloride on large scale
  • Method for preparing tropisetron hydrochloride on large scale

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Embodiment Construction

[0024] (1) Preparation of indole-2-carbonyl chloride:

[0025] Add 20.0g of indole-3-carboxylic acid, 300mL of 1,2-dichloroethane and 3 mL of DMF into a 500mL three-neck flask, slowly add 20 mL of thionyl chloride dropwise under stirring, react at 45°C for 8h, and evaporate excess Thionyl chloride and 1,2-dichloroethane were dissolved in 100 mL tetrahydrofuran for later use.

[0026] (2) Preparation of α-tropine sodium:

[0027] Add 19.0g of α-tropine alcohol, 100mL of tetrahydrofuran and 5.4g of NaOH solid into a 500 mL three-neck flask, stir and react at room temperature for 4h, and set aside.

[0028] (3) Preparation of Tropisetron Hydrochloride:

[0029] Slowly add the THF solution of indole-3-formyl chloride to the THF solution of sodium tropinate at room temperature, stir and react at 35°C overnight, recover THF by distillation under reduced pressure, and recrystallize with 95% ethanol to obtain a light yellow solid. Add 70 mL of absolute ethanol, heat to dissolve, pa...

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Abstract

The invention relates to a method for preparing tropisetron hydrochloride on large scale, which comprises the steps that: indole-3-formic acid reacts with thionyl chloride in 1,2-dichloroethane, so indole formyl chloride is obtained, 1,2-dichloroethane and thionyl chloride are removed by reduced pressure distillation, and tetrahydrofuran solution is added; under the condition that tetrahydrofuran exists, alpha-tropine reacts with sodium hydroxide to obtain alpha-tropine sodium salt; the tetrahydrofuran solution of the indole formyl chloride reacts with the tetrahydrofuran solution of the alpha-tropine sodium salt, so tropisetron is obtained; and finally, the tropisetron reacts with hydrochloric acid, and the high-purity tropisetron hydrochloride is prepared after purification.

Description

technical field [0001] The invention belongs to the production field of fine chemical products, and in particular relates to a preparation process of tropisetron hydrochloride, which is used for producing antiemetic medicines. Background technique [0002] The chemical name of Tropisetron hydrochloride is endo-1H-indole-3-carboxylic acid-8-methyl-azabicyclo[3.2.1]oct-3-yl ester hydrochloride, which is highly Selective 5-HT3 receptor antagonist, suitable for the prevention and treatment of nausea and vomiting after chemotherapy, radiotherapy and surgery for cancer in children and adults, its chemical structure is shown in figure 1 . [0003] As an existing preparation method, in U.S. Patents (US3980668, US4789673, US4797406, US4803199), the reaction of indole-3-carboxylic acid with oxalyl chloride is described, and the treatment with dichloromethane and n-hexane gives 3-indolecarbonyl chloride, and then It reacts with the lithium tropine alkoxide generated by tropine alcoho...

Claims

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Application Information

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IPC IPC(8): C07D451/12
Inventor 杨俊吴锋向红琳张静陈敏朱敏甘丽红陈锋
Owner 湖南康普医药研究院
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