Method for preparing 2-(7-methoxy-1-naphthyl) ethylamine industrially

A methoxy and naphthyl technology, applied in the field of preparation of 2-ethylamine, can solve the problems of difficult purification, unfavorable large-scale industrial production, high requirements for production equipment, etc., and achieves improved product yield, safety and simple post-processing , reducing the effect of post-processing steps

Inactive Publication Date: 2014-06-18
SHANGHAI INST OF PHARMA IND CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] In the hydrogenation reaction where formula VIII is converted into formula (I), a high pressure of 30 bar and a high temperature of 40 degrees are used, which requires too much production equipment and is not conducive to large-scale industrial production
And it is also accompanied by the generation of by-products such as formula (XIII), which are similar in nature and difficult to purify

Method used

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  • Method for preparing 2-(7-methoxy-1-naphthyl) ethylamine industrially
  • Method for preparing 2-(7-methoxy-1-naphthyl) ethylamine industrially
  • Method for preparing 2-(7-methoxy-1-naphthyl) ethylamine industrially

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Experimental program
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Effect test

Embodiment 1

[0022] Dissolve compound VIII (1.97g) in ethanol (30ml), add Raney-Ni (0.5g) dissolved in ethanol, cool to 10 degrees, add potassium borohydride (0.54g) in batches, remove the ice bath, and react at room temperature After 23 hours, the substrate disappeared, the solvent was removed by concentration under reduced pressure, and ethyl acetate (30ml) was added for extraction; the organic phase was washed with acid, alkali, saturated brine, and concentrated to obtain the final product. Yield: 95%.

Embodiment 2

[0024] Dissolve compound VIII (9.85g) in methanol (150ml), add Raney-Ni (3g) dissolved in ethanol, cool to 10 degrees, add potassium borohydride (2.7g) in batches, remove the ice bath, and react at room temperature for 18 After hours, the substrate disappeared, the solvent was removed by concentration under reduced pressure, and ethyl acetate (150ml) was added for extraction; the organic phase was washed with acid, alkali, saturated brine, and concentrated to obtain the final product. Yield: 93%.

Embodiment 3

[0026] Dissolve compound VIII (1.97g) in ethanol (30ml), add Raney-Ni (0.6g) dissolved in ethanol, cool to 0℃ in an ice bath, add potassium borohydride (0.54g) in batches, and react at 0℃ for 28 After hours, the substrate disappeared, the solvent was removed by concentration under reduced pressure, and ethyl acetate (30ml) was added for extraction; the organic phase was washed with acid, alkali, saturated brine, and concentrated to obtain the final product. Yield: 92%.

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Abstract

The invention belongs to the technical field of a preparation method for 2-(7-methoxy-1-naphthyl) ethylamine. In an organic solvent, a compound in a formula (VIII) is reacted under the action of Raney-Ni and hydroboron to form the 2-(7-methoxy-1-naphthyl) ethylamine. The method solves the problem that reaction conditions of high pressure and heating are required in the conventional reports, and a preparation method which has mild reaction conditions, only needs normal temperature and normal pressure and does not have any special requirement on reaction equipment and staff is provided; in addition, by the method, byproducts are absent, the product purifying difficulty is greatly reduced, aftertreatment steps are reduced, and the product yield is improved; and during the whole reaction, the operation is safe, the aftertreatment is simple, the controllability is high, and the purity and yield are high; and compared with the conventional process, the method is more suitable for industrial production.

Description

Technical field [0001] The invention belongs to the technical field of preparation methods of 2-(7-methoxy-1-naphthyl)ethylamine. Background technique [0002] Agomelaline, whose chemical name is N-[2-(7-methoxy-1-naphthyl)ethyl]acetamide, and its trade name is Valdoxan. It has a dual effect, not only the melatonin energy Agonists of system receptors also have the effect of antagonizing 5HT2C receptors. Its properties make it active in the central nervous system, especially in severe depression, seasonal affective disorder, sleep disorders, cardiovascular diseases, digestive system diseases, flying It is active in the treatment of insomnia and fatigue caused by jet lag, appetite disturbance and obesity. It is the first melatonin antidepressant, which can effectively treat depression, improve sleep parameters and maintain sexual function. [0003] The compound represented by formula (I) is an important intermediate for the synthesis of agomelatine. A method for preparing agomelati...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C217/60C07C213/02
Inventor 张鹏单汉滨袁哲东蒋旭东黄雨俞雄
Owner SHANGHAI INST OF PHARMA IND CO LTD
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