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Process for preparing 1-[2-amino(p-methoxyphenyl)ethyl]cyclohexanol

A technology of methoxyphenyl and cyclohexanol, applied in chemical instruments and methods, preparation of organic compounds, preparation of aminohydroxy compounds, etc., can solve the problems of high production cost, difficult control, large exothermic heat, etc. The effect of preparation cost, low price and mild reaction conditions

Inactive Publication Date: 2015-11-25
JINGCHU UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This method requires a large amount of sodium borohydride, and a large amount of heat is released during the feeding process, which is not easy to control. After-treatment, a large amount of acid is required to destroy unreacted sodium borohydride, the production cost is too high, and it has a very adverse impact on production and the environment.
[0005] Chinese Journal of Pharmaceutical Industry, 2004,35,577 introduced a new reduction process: use tetrahydrofuran as solvent, utilize Red-Al as reducing agent, reduction preparation 1-[2-amino (p-methoxyphenyl) ethyl ] cyclohexanol, this method still has the price of reductant more expensive, causes problems such as production cost is higher

Method used

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Examples

Experimental program
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Effect test

Embodiment 1

[0016] In a 10L three-necked flask, add 241g of 1-[cyano(p-methoxyphenyl)methyl]cyclohexanol, add 2000g of methanol, turn on the temperature and stir to dissolve. Prepared Raney nickel catalyst 20g, hydrazine hydrate (N 2 h 4 ·H 2 O, 50%) 250g, heat up to 55-60°C, react for 4h, filter, concentrate the filtrate to dryness under reduced pressure at 40°C, cool to the internal temperature below 30°C, add 2000g of purified water, add concentrated hydrochloric acid dropwise, adjust pH = 2 -3. After stirring for 20 minutes, re-test the pH value unchanged, extract the reaction solution 3 times with 1200g ethyl acetate, combine the water layer, adjust the pH to 9-10 with 10% potassium hydroxide solution, and continue stirring for 20 minutes. The pH value was re-tested unchanged, and the aqueous layer was extracted three times with 1200g ethyl acetate, the organic layers were combined, dried with anhydrous sodium sulfate, and concentrated to dryness under reduced pressure at 60-70°C t...

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Abstract

The invention relates to a method for preparing venlafaxine. The method comprises the steps of: by taking 1-[cyan-(p-methoxylphenyl)methyl]cyclohexanol as a raw material, in the temperature range from 40 to 80DEG C, performing reduction reaction in the presence of a catalyst by taking low-grade alcohol or low-grade alcohol mixture solvent as a solvent and hydrazine hydrate as a reductant, thus obtaining 1-[2-amino(p- methoxylphenyl)ethyl]cyclohexanol. The method has the advantages that the cyan reduction reaction is mild in conditions, the solvent adopts commonly-used low-grade alcohol or alcohol-water mixture solvent, especially the hydrazine hydrate serves as a reductant, and is lower in cost compared with other reductants, and cheap raney nickel is directly adopted as the catalyst, so that the preparation cost can be greatly lowered.

Description

technical field [0001] The present invention relates to the technical field of preparation methods of pharmaceutical intermediates, in particular to a method for preparing an antidepressant drug venlafaxine intermediate 1-[2-amino(p-methoxyphenyl)ethyl]cyclohexanol . Background technique [0002] Venlafaxine, whose chemical name is 1-[2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]cyclohexanol, is a new type of antidepressant, which began to be used in my country in 1997 In clinical application, it is widely used in the treatment and prevention of emotional disorders, such as depression, mania, inattention, hyperexcitability, parkinsonism, epilepsy, brain dysfunction, dementia and related disorders. Since venlafaxine has been widely used as an antidepressant with relatively definite curative effect, especially in the industrialized production in pharmaceutical manufacturing enterprises, it is necessary to consider the technological conditions of the product, that is, the require...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C217/74C07C213/02
Inventor 罗磊李立威李立
Owner JINGCHU UNIV OF TECH