Preparation of agomelatine intermediate 2-(7-methoxy-1-naphthyl) acetamide

A methoxy and acetamide technology, applied in the field of preparation of 2-acetamide, can solve the problems of incomplete, unsuitable for industrial production, difficult to purify pure products, etc., and achieves cost saving, mild reaction conditions, and reaction yield. high effect

Inactive Publication Date: 2009-07-22
SHANGHAI INST OF PHARMA IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At the same time, this step needs to use benzene as a solvent, which does not meet the requirements of industrialized production in consideration of environmental factors
[0010] (3) Subsequent steps of aromatization of ethyl (7-methoxy-3,4-dihydro-1-(2H)-naphthalenyl)acetate are often incomplete, and after saponification a mixture is obtained which is difficult Purification affords pure product (V)

Method used

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  • Preparation of agomelatine intermediate 2-(7-methoxy-1-naphthyl) acetamide
  • Preparation of agomelatine intermediate 2-(7-methoxy-1-naphthyl) acetamide
  • Preparation of agomelatine intermediate 2-(7-methoxy-1-naphthyl) acetamide

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Experimental program
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Effect test

Embodiment 1

[0024]

[0025] Compound B 1 (50g), dichlorodicyanobenzoquinone (DDQ) (105g) was dissolved in glacial acetic acid (200ml), and reacted by heating at 80°C. When all starting substrate had disappeared, it was cooled to room temperature and filtered. The acetic acid was removed by evaporation to give the desired product. Yield: 89%.

Embodiment 2

[0027]

[0028] Compound B 2 (50g), DDQ (105g) was dissolved in glacial acetic acid (200ml), and the temperature was raised to 80°C for reaction. When all starting substrate had disappeared, it was cooled to room temperature and filtered. Concentrate under reduced pressure to remove acetic acid to obtain the target product. Yield: 88%.

Embodiment 3

[0030]

[0031] Compound B 3 (5g), DDQ (10.5g) was dissolved in glacial acetic acid (20ml), heated to 80°C for reaction. When all starting substrate had disappeared, it was cooled to room temperature and filtered. Concentrate under reduced pressure to remove acetic acid to obtain the target product. Yield: 84%.

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Abstract

The invention relates to a preparation method for an intermediate compound for preparing agomelatine. The agomelatine intermediate 2-(7-methoxyl-1-naphthyl) acetamide is directly obtained by the ammonolysis of (7-methoxyl-1-naphthyl) ethyl acetate. The method has high reaction yield; reagents used have low cost; the method also has relatively mild reaction condition, safe operation and good controllability. Besides, the whole reaction process is not added with highly toxic reagent or solvent, thus meeting the requirement of environmental protection and being very suitable for industrialized production application.

Description

technical field [0001] The invention relates to a preparation method of 2-(7-methoxy-1-naphthyl)acetamide. Background technique [0002] Agomelatine (agomelatine), chemical name N-[2-(7-methoxy-1-naphthyl) ethyl] acetamide, trade name Valdoxan, its structural formula is as follows: [0003] [0004] Agomelatine has a dual action, not only an agonist of receptors of the melatoninergic system, but also an antagonist of 5HT2C receptors, and its properties make it active in the central nervous system, especially in major depression, seasonal Active in the treatment of affective disorders, sleep disorders, cardiovascular diseases, digestive disorders, jet lag-induced insomnia and fatigue, appetite disorders and obesity. It is the first melatonin-class antidepressant to be effective in treating depression, improving sleep parameters and maintaining sexual function. [0005] The compound shown in formula (VII) is an important intermediate 2-(7-methoxy-1-naphthyl)acetamide for ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C235/34C07C231/02
CPCY02P20/55
Inventor 张鹏单汉滨袁哲东黄雨程兴栋俞雄
Owner SHANGHAI INST OF PHARMA IND
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