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Preparation method of 7-methoxy-1-naphthylethylamine

A methoxy, naphthylethylamine technology is applied in the field of preparation of a key intermediate 7-methoxy-1-naphthaleneethylamine, and achieves the effects of low cost of raw materials, avoiding high temperature and high pressure reactions, and reducing environmental pollution problems

Inactive Publication Date: 2012-07-25
湖北万知化工医药股份有限公司
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Problems solved by technology

And the synthetic method of intermediate 7-methoxyl group-1-naphthaleneacetonitrile often has environmental problems or severe reaction condition restriction such as low temperature or high pressure reaction, as CN101735091A, the synthetic method of 7-methoxyl group-1-naphthaleneacetonitrile reported in US5194614 method

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  • Preparation method of 7-methoxy-1-naphthylethylamine

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Embodiment 1

[0022] A preparation method of 7-methoxy-1-naphthylethylamine, the steps are as follows:

[0023] 1, the preparation of 7-methoxy-1-naphthyl alcohol

[0024] Dissolve 24g of ethyl 7-methoxy-1-naphthaleneacetate in a mixture of 50mL of water and 80mL of ethanol, stir mechanically, add 13.3g of sodium borohydride, and reflux for 2 hours. TLC shows that the reaction is complete, cool to room temperature, and add 200mL of water, extracted twice from water with 300mL ethyl acetate respectively, combined ethyl acetate, washed once with water, once with saturated ammonium chloride solution, once with saturated brine, and spin-dried to obtain 15g of yellow solid. It was confirmed to be 7-methoxy-1-naphthyl alcohol with a melting point of 82-84°C and a yield of 74%.

[0025] 2, Preparation of 7-methoxyl-1-naphthyl ethyl methanesulfonate

[0026] Add 11g of 7-methoxy-1-naphthyl alcohol and 11g of triethylamine obtained in step 1 into a 250mL three-necked flask, add 80mL of dichloromet...

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Abstract

The invention belongs to the technical field of pharmaceutical intermediates, and in particular relates to a new preparation method of a key intermediate, 7-methoxy-1-naphthylethylamine of a pharmaceutical ingredient, agomelatine. The aim of the invention is to reduce the cost, optimize the process and bring convenience to the industrial production. The preparation method comprises the following steps: taking 7-methoxy-1-naphthylacetate as a raw material; reducing by sodium borohydride to obtain 7-methoxy-1-naphthaleneethanol; carrying out a methyl sulfonylation reaction to obtain 7-methoxy-1-naphthylethylmethanesulfonate; reacting 7-methoxy-1-naphthylethylmethanesulfonate with a phthalimide potassium salt to obtain 7-methoxy-1-(N-phthalimidoethyl)naphthyl; and finally hydrolyzing 7-methoxy-1-(N-phthalimidoethyl)naphthyl to obtain the product, 7-methoxy-1-naphthylethylamine. The preparation method has the advantages of being simple and convenient in operation, reasonable in reaction process, low in production cost, good in product quality, high in purity (above 98%), having no environment pollution and being suitable for industrial production.

Description

technical field [0001] The invention relates to the technical field of synthesis of pharmaceutical intermediates, in particular to a preparation method of 7-methoxy-1-naphthylethylamine, a key intermediate of agomelatine. Background technique [0002] Agomelatine, the first melatonin receptor agonist, has a good antidepressant effect and was approved for marketing in Europe in May 2009. 7-methoxyl-1-naphthylethylamine is the most critical intermediate for the preparation of agomelatine, so its market prospect and economic benefits have great potential. [0003] The synthesis method route of 7-methoxyl-1-naphthylethylamine in existing literature reports is mainly to obtain the final product through the reduction of the intermediate 7-methoxyl-1-naphthylacetonitrile. And the synthetic method of intermediate 7-methoxyl group-1-naphthaleneacetonitrile often has environmental problems or severe reaction condition restriction such as low temperature or high pressure reaction, as ...

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Application Information

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IPC IPC(8): C07C217/60C07C213/02
Inventor 孙大成周叶兵鲁东安张圣波
Owner 湖北万知化工医药股份有限公司
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