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Preparation method of venlafaxine impurity E

An impurity and substance technology, applied in the field of preparation of venlafaxine impurity E, can solve the problems of waste water, solid waste, complicated treatment, low purity and yield, etc., and achieves convenient industrial production, simple post-processing, and product purity. high effect

Inactive Publication Date: 2020-09-18
SUZHOU NO 4 PHARMA FACTORY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] ①The synthesis steps are long, requiring 5 steps to react;
[0006] ② low purity and yield;
[0007] ③Using hydrogenation equipment, high temperature and high pressure, high risk;
[0009] ⑤ The post-processing of the whole process is complicated, producing more waste water and solid waste, and the environment is not friendly

Method used

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  • Preparation method of venlafaxine impurity E
  • Preparation method of venlafaxine impurity E
  • Preparation method of venlafaxine impurity E

Examples

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preparation example Construction

[0024] The method for preparing venlafaxine impurity E of the present invention includes:

[0025] (1) Condensation reaction: Dissolve 4-methoxybenzeneacetonitrile (A) in ethanol, strengthen alkali to make the solution alkaline, add cyclohexanone, react at 15-30℃ for 4~5h, then use acid Adjust the pH to 5-7 and quench, and the product is filtered and dried to obtain 1-[2-cyano-1-(4-methoxyphenyl)ethyl]cyclohexanol (B);

[0026] (2) Reduction reaction: add aluminum trichloride and sodium borohydride to the solvent tetrahydrofuran, stir for 1h, add 1-[2-cyano-1-(4-methoxyphenyl)ethyl obtained in step (1) Cyclohexanol (B), reflux reaction for 3~4h, add acid to quench, extract with ethyl acetate, and distill the oil phase to obtain 1-[2-amino-1-(4-methoxyphenyl)ethyl ]Cyclohexanol (C);

[0027] (3) Ring-forming reaction: add formic acid and formaldehyde to the 1-[2-amino-1-(4-methoxyphenyl)ethyl]cyclohexanol (C) obtained in step (2), at 50~ After reacting at 80°C for 2 to 3 hours, the...

Embodiment 1～5

[0031] The specific reaction conditions and liquid phase purity of Examples 1 to 5 are as follows:

[0032]

[0033] It can be seen from the above table that the liquid phase purity of the present invention is greater than or equal to 99%, the method for synthesizing venlafaxine impurity E has fewer steps and higher product purity. The method avoids the use of high-pressure hydrogenation equipment and dangerous chemical reagents, and has high safety. In addition, there is less waste liquid, simple post-reaction treatment, convenient operation, and convenient industrial production.

[0034] Step (1) The strong base is sodium hydroxide, and the amount ratio to 4-methoxybenzeneacetonitrile is 1:1. Step (1) The ratio of cyclohexanone to 4-methoxybenzeneacetonitrile is 1 to 3:1. In the step (2), the amount ratio of aluminum trichloride to 1-[2-cyano-1-(4-methoxyphenyl)ethyl]cyclohexanol is 2.2-5.5:1, boron The ratio of sodium hydride to 1-[2-cyano-1-(4-methoxyphenyl)ethyl]cyclohexano...

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Abstract

The invention belongs to the technical field of organic synthesis, and relates to a preparation method of venlafaxine impurity E. The preparation method comprises the following steps: (1) a condensation reaction; (2) a reduction reaction; and (3) a cyclization reaction. The method has the advantages of fewer steps for synthesizing the venlafaxine impurity E, higher product purity, safety in reaction, less waste liquid, simple post-treatment, convenience in operation and convenience in industrial production.

Description

Technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a method for preparing venlafaxine impurity E. Background technique [0002] Venlafaxine impurity E (Venlafaxine-4, (5RS)-5-(4-Methoxyphenyl)-3-methyl-1-oxa-3-azaspiro-[5.5]undecane) is a pharmaceutical intermediate with the molecular formula C 17 H 23 N 2 . This substance is generally used as a synthetic salt of hydrochloric acid. According to the venlafaxine impurity E in the European Pharmacopoeia, the synthetic route is as follows: [0003] [0004] However, this process has the following disadvantages: [0005] ①The synthesis step is long and requires 5 steps of reaction; [0006] ②Low purity and yield; [0007] ③The use of hydrogenation equipment, high temperature and high pressure, high risk; [0008] ④Use dangerous reagents such as borane, and use second-class solvents such as toluene; [0009] ⑤The post-processing of the whole process is complicated, resulting in a lot of ...

Claims

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Application Information

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IPC IPC(8): C07D265/02
CPCC07D265/02
Inventor 刘俊银
Owner SUZHOU NO 4 PHARMA FACTORY
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