Method for preparing Zolmitriptan

A technology of zolmitriptan and oxazolidinone, which is applied in the field of preparation of zolmitriptan, can solve the problems of low molar yield, high cost of zolmitriptan, and time-consuming, etc., and achieve The effect of reducing production cost and being suitable for industrial production

Inactive Publication Date: 2010-04-14
SUZHOU LEADER CHEM
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Problems solved by technology

[0008] 1. In the production process, highly toxic phosgene is used, which increases the danger of production;
[0009] 2. In the reduction step of aniline, stannous chloride or sodium sulfate is used as a reducing agent, the former is not easy to filter, and has great environmental p

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  • Method for preparing Zolmitriptan
  • Method for preparing Zolmitriptan
  • Method for preparing Zolmitriptan

Examples

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Embodiment Construction

[0026] The following are specific examples of the present invention to further describe the technical solution of the present invention, but the present invention is not limited to the examples.

[0027] A preparation method of zolmitriptan, comprising the steps of:

[0028] (1) Nitration reaction: In a 5L three-necked flask, add 1450ml of concentrated sulfuric acid (95% to 98%) into 325ml of water to form an 80% sulfuric acid solution, and add 1KG (6.06mol) L in batches under stirring below 30°C -Phenylalanine, after adding, stir and heat up to complete dissolution (about 30°C), cool in an ice-salt bath to 0°C, slowly add 420g of concentrated nitric acid dropwise, control the temperature at 5°C, after dropping, stir at 5°C for 2h, Stir at 20°C to 30°C for 2 hours, at 40°C to 50°C for 2 hours, cool to room temperature, pour the reaction solution into 10L of ice water, stir, and below 20°C, adjust the pH to 6.3 with about 4.2L of 25% ammonia water, and cool to 0°C, keep 1h, fi...

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Abstract

The invention relates to a method for preparing Zolmitriptan, which comprises the following steps: (1) obtaining a mixed solution containing (S)-4-(4-hydrazinobenzyl)-2-oxazolidinone by sequentially conducting diazotization reaction, reduction reaction and hydrolysis reaction on (S)-4-(4- aminobenzyl)-2-oxazolidinone; and (2) leading the (S)-4-(4-hydrazinobenzyl)-2-oxazolidinone in the mixed solution obtained in the step (1) and the dimethylamine butyral to carry out fisher-indole reaction so as to generate the Zolmitriptan, wherein in the step (2), the fisher-indole reaction is kept under the condition with the pH of 3-5. Compared with the prior art, the preparation method has the advantages that the molar yield is improved to 55%, the production cost of the Zolmitriptan is low and the preparation method is more applicable to industrial production.

Description

technical field [0001] The invention belongs to the field of organic chemistry and medicinal chemistry, in particular to a preparation method of zolmitriptan. Background technique [0002] Zolmitriptan (zolmitriptan), chemical name (S)-4-[[3-[2-(dimethylamino)ethyl]-1H-indol-5-yl]methyl]-2-oxa Oxazolidinone has the following structural formula: [0003] [0004] Zolmitriptan is a highly selective and potent 5-HTIB / ID receptor agonist. It is used for the treatment of migraine. It can not only relieve headache quickly, but also relieve photophobia, sound fear, nausea, etc. complication. It is of great significance to study the synthesis of zolmitriptan. [0005] Zolmitriptan is mainly prepared by the following route in the prior art: [0006] [0007] There are following deficiencies in the above-mentioned route: [0008] 1. In the production process, highly toxic phosgene is used, which increases the danger of production; [0009] 2. In the reduction step of anili...

Claims

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Application Information

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IPC IPC(8): C07D413/06
Inventor 郑丽玲李明蓉宋桃菊许伟
Owner SUZHOU LEADER CHEM
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