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A kind of preparation method of venlafaxine hydrochloride intermediate

A technology of venlafaxine hydrochloride and intermediates, which is applied in the field of medicine, can solve the problems of dangerous reaction, low yield, difficult post-processing, etc., and achieve the effects of easy industrial production, safe and controllable operation, and enhanced catalytic effect

Active Publication Date: 2018-10-30
山东安信制药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In Chinese patent 200410002726.5, red aluminum is used as reducing agent to prepare 1-[2-amino-1-(4-methoxyphenyl) ethyl] cyclohexanol, and the yield is as high as 92%, but red aluminum is expensive and reactive The solvent THF is difficult to recover, and the total cost is high
However, high-temperature hydrogenation equipment is required, the reaction is more dangerous, and the catalyst is not easy to recycle
[0008] In summary, in the currently disclosed methods for the preparation of 1-[2-amino-1-(4-methoxyphenyl)ethyl]cyclohexanol, there are expensive and dangerous reducing agents or reduction catalysts, post- Difficult to handle, low yield, etc., not suitable for large-scale production

Method used

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  • A kind of preparation method of venlafaxine hydrochloride intermediate
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  • A kind of preparation method of venlafaxine hydrochloride intermediate

Examples

Experimental program
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Effect test

Embodiment 1

[0032] 1) Preparation of feed solution: Dissolve 100g of 1-cyano-[(4-methoxyphenyl)methyl]cyclohexanol in 200ml of toluene, stir to dissolve, and obtain a feed solution for later use.

[0033] 2) Microreactor reaction: Install the Raney nickel screen at the pipe connection, use nitrogen to fully replace the air in the reaction zone of the microreactor, then preheat the reaction zone of the microreactor to an internal temperature of 30°C, and then pass Enter the hydrogen gas to control the pressure of 0.2-0.3MPa, and inject the feed liquid in step 1) into the reaction zone of the microreactor through the slurry pump to control the temperature at 30°C for 3-8s; Water cooling) after cooling, collect reaction solution;

[0034] 3) Generation of 1-[2-amino-1-(4-methoxyphenyl)ethyl]cyclohexanol sulfate: the reaction solution was cooled to room temperature, filtered to remove insoluble matter, and slowly added dropwise to the filtrate 11.5ml Concentrated sulfuric acid (18mol / L), slo...

Embodiment 2

[0036] 1) Preparation of slurry: Dissolve 100g of 1-cyano-[(4-methoxyphenyl)methyl]cyclohexanol in 200ml of ethyl acetate, stir to dissolve, and obtain a feed solution for later use;

[0037]2) Microreactor reaction: Install the Raney nickel screen at the pipe connection, use nitrogen to fully replace the air in the reaction zone of the microreactor, preheat the microreactor to an internal temperature of 40°C, and inject hydrogen to control the reaction. The pressure is 0.3-0.4MPa, the feed liquid is pumped into the microreactor by the slurry pump, and the temperature is controlled in the reaction area at 40°C for 1-5s; after the reaction is completed, it is cooled by the cooling area (the cooling area is cooled by circulating water), Collect the reaction solution;

[0038] 3) Generation of 1-[2-amino-1-(4-methoxyphenyl)ethyl]cyclohexanol sulfate: the reaction solution was cooled to room temperature, filtered to remove insoluble matter, and slowly added dropwise to the filtrat...

Embodiment 5

[0042] Preparation of venlafaxine hydrochloride

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Abstract

The invention discloses a preparation method of a venlafaxine hydrochloride intermediate. The preparation method comprises the following steps of in a micro-reactor loaded with a raney nickel screen net catalyst, enabling a compound I and hydrogen to react at the temperature of 20 to 40 DEG C, so as to obtain a compound II; adding the compound II into sulfuric acid, and forming salt, so as to obtain a target product, namely 1-[2-amino-1-(4-methoxyphenyl)ethyl]cyclohexanol sulfate (compound III). The preparation method has the advantages that on the basis of the original micro-reactor, the raney nickel screen net catalyst is creatively clamped to the connecting part of a pipeline, so that the catalyzing effect is enhanced, and the catalyst can be recycled; the damage to a slurry pump of the micro-reactor and the blockage of a reaction pipeline due to mixing of the catalyst into material liquid are avoided.

Description

technical field [0001] The invention relates to a preparation method of venlafaxine hydrochloride intermediate 1-[2-amino-1-(4-methoxyphenyl)ethyl]cyclohexanol sulfate, belonging to the technical field of medicine. Background technique [0002] Venlafaxine hydrochloride, chemical name: 1-[2-(dimethylamine)-1-(4-methoxyphenyl)ethyl]cyclohexanol hydrochloride, molecular formula: C 17 h 27 NO 2 HCl; molecular weight: 313.86, structural formula as follows: [0003] [0004] Venlafaxine hydrochloride is a phenethylamine antidepressant developed by Wyeth-Ayerst Company of the United States. Its main function is to inhibit the reuptake of 5-hydroxytryptamine and norepinephrine, and also slightly inhibit the reuptake of DA. Its main metabolite O-desvenlafaxine also has the above effects. Since its clinical application, venlafaxine hydrochloride was initially used to treat depression, and later also used to treat obsessive-compulsive disorder and anxiety disorder. [0005] At...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C213/02C07C217/74
CPCY02P20/584
Inventor 江海平杨庆坤杨波勇周学文李保勇吴柯张兆珍董廷华吴兆申高大龙
Owner 山东安信制药有限公司
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