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Novel method for preparing agomelatine

A concentrated sulfuric acid, slow technology, applied in the field of industrial production of agomelatine, can solve the problems of environmental pollution, many steps, complex route and process, and achieve the effects of reducing pollution, mild reaction conditions and easy operation.

Active Publication Date: 2014-06-18
FUJIAN COSUNTER PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0015] The above-mentioned routes are complex in process, with many steps, and pollute the environment. Therefore, it is still of great significance to study new synthetic routes, especially those with simple steps, easy production and operation, and less environmental pollution.

Method used

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  • Novel method for preparing agomelatine
  • Novel method for preparing agomelatine
  • Novel method for preparing agomelatine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Take 10ml of concentrated sulfuric acid in a 50ml flask, slowly add 10g of 7-methoxy-1-naphthylacetonitrile under stirring, after stirring evenly, control the stirring reaction at 50°C for 2h, TLC tracking until there is no starting material in the reaction, the reaction is complete. After natural cooling, slowly pour it into 100ml of ice water, then adjust the pH to neutral and slightly alkaline with concentrated ammonia water, and precipitate a solid, filter, wash the filter cake with a little water, and dry to obtain 9.8g of white solid (7-methoxy -1-naphthyl)acetamide, yield 89.8%, melting point: 135-138°C.

[0038] Take the above (7-methoxy-1-naphthyl)acetamide solid 7.2g, sodium borohydride 3.2g, aluminum trichloride 15g, tetrahydrofuran 100ml into the reaction flask, reflux reaction until the substrate disappears. Add dilute hydrochloric acid, extract twice with ethyl acetate, adjust the aqueous layer to alkaline with ammonia water, then extract twice with ethyl ...

Embodiment 2

[0043] Take 15ml of concentrated sulfuric acid in a 50ml flask, slowly add 20g of 7-methoxy-1-naphthylacetonitrile under stirring, after stirring evenly, control the stirring reaction at 50°C for 2h, TLC tracking until there is no starting material in the reaction, the reaction is complete. After cooling down naturally, slowly pour it into 200ml of ice water, then adjust the pH to neutral and slightly alkaline with concentrated ammonia water, and precipitate a solid, filter, wash the filter cake with a little water, and dry to obtain 20g of white solid (7-methoxy- 1-naphthyl)acetamide, yield 91.6%, melting point: 135-138°C.

[0044] Take 18g of the above (7-methoxy-1-naphthyl)acetamide solid, 8g of sodium borohydride, 37g of aluminum trichloride, and 200ml of tetrahydrofuran into the reaction flask, and reflux until the substrate disappears. Add dilute hydrochloric acid, extract twice with ethyl acetate, adjust the aqueous layer to alkaline with ammonia water, then extract twi...

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Abstract

The invention relates to preparation of antidepressants, in particular to a novel method for preparing agomelatine. The novel method includes step one, heating 7-methoxy-1-naphthylacetonitrile under acidic condition, and pouring to water to obtain 2- (7-methoxy-1-naphthyl) acetamide; and step two, generating 2- (7-methoxy-1-naphthyl) ethylamine under conditions of reducing agent and lewis acid by the 2- (7-methoxy-1-naphthyl) acetamide obtained in the step one, and directly performing acetylation without purification under conditions of acid-binding agent and acetylation reagent to obtain N- (2- (7-methoxy-1-naphthyl) ethyl) acetamide (agomelatine).

Description

technical field [0001] The invention relates to the technical field of a new method for industrially producing agomelatine. Background technique [0002] Agomelatine (agomelatine), chemical name is N-[2-(7-methoxy-1-naphthyl) ethyl] acetamide, and its structural formula is as shown in formula (I). Its trade name is Valdoxan, which is the first melatonin antidepressant developed by Servier in France, and it was launched in Germany and the UK in 2009. It can effectively treat depression, improve sleep parameters and maintain sleep quality. features of sexual function. [0003] [0004] Agomelatine has dual properties. On the one hand, it is an agonist of the melatonin receptor; on the other hand, it is an antagonist of the 5-HT2C receptor. These properties make it central nervous system active, especially in the treatment of major depression, seasonal affective disorder, sleep disorders, cardiovascular conditions, digestive system conditions, insomnia and fatigue due to j...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C233/18C07C231/02
Inventor 姚建堤陈首鹤陈仕魁杨喜鸿苏葳
Owner FUJIAN COSUNTER PHARMA CO LTD
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