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Preparation method of piperazine compound and intermediate thereof

A compound and intermediate technology, applied in the field of drug synthesis, can solve the problems of cumbersome post-processing, low production cost, and low yield

Inactive Publication Date: 2012-11-21
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0016] The purpose of the present invention is to provide some new methods for preparing piperazine compounds against the defects of the prior art methods. These methods have low production costs and overcome the shortcomings of long reaction time, cumbersome post-treatment and low yield.

Method used

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  • Preparation method of piperazine compound and intermediate thereof
  • Preparation method of piperazine compound and intermediate thereof
  • Preparation method of piperazine compound and intermediate thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0172] Example 1 Preparation of 2-methoxyphenylpiperazine (SL-1)

[0173]

[0174] Dissolve 32mL (0.44mol) of thionyl chloride in 80mL of chloroform solution, place it in a three-neck flask equipped with a condensing reflux tube and an ice-water bath, stir mechanically, and absorb the tail gas with water. Slowly add a mixed solution of 19.2mL (0.2mol) diethanolamine and 30mL chloroform dropwise with a constant pressure funnel. During the dropwise addition, control the reaction temperature not to exceed 30°C, and the dropwise addition time is 3h. After the dropwise addition, remove the ice-water bath, react at room temperature for 1 hour, then slowly raise the temperature, wait until the solid is completely dissolved and raise the temperature to 60°C, continue the reaction for 0.5 hour, stop heating, cool to room temperature, and suction filter to obtain bis(2-chloroethyl ) amine hydrochloride white powdery solid 34.4g, yield 96.4%, no further purification, directly used in ...

example 2

[0177] The preparation of example 2 4-methoxyphenylpiperazine (SL-2)

[0178]

[0179] Add 5.6mL (0.05mol) of 4-methoxyaniline, 8.925g (0.05mol) of bis(2-chloroethyl)amine hydrochloride, and 10.6g (0.1mol) of sodium carbonate in a 250mL three-necked flask , 1.0g of catalyst and 80mL of distilled water, reflux at 100°C for 24h, after the reaction is complete, after cooling, extract twice with ethyl acetate (2×30mL), combine the organic phases, and wash with 20mL of saturated brine, and wash the organic layer with anhydrous Dry over sodium sulfate, filter, and concentrate under reduced pressure. Add a certain amount of hydrogen chloride ether solution to the crude product, and solids begin to appear. The resulting solids are recrystallized with isopropanol and n-hexane to obtain coffee 4-methoxyphenylpiperazine Hydrochloride color solid 8.9g, the preparation method of 4-methoxyphenylpiperazine is consistent with Example 1, and the total yield (calculated as 4-methoxyaniline) ...

example 3

[0180] The preparation of example 3 phenylpiperazine (SL-3)

[0181]

[0182] The preparation method was the same as in Example 1, and 2-methoxyaniline was replaced by aniline to obtain 12.6 g of phenylpiperazine with a total yield of 77.8%.

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PUM

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Abstract

The invention discloses a preparation method of a piperazine compound and an intermediate thereof, belonging to the field of medicine synthesis. The compound and the intermediate thereof can be used for preparing medicines for treating central nervous system disease, such as analgetics, medicines for drug addiction, medicines for schizophrenia, medicines for parkinson disease, etc. The preparation method disclosed herein has the advantages of high reaction yield, short reaction time, easy obtainment and cheap raw materials, convenient product separation and purification, easy control of reaction, little generation of three wastes, low risk, etc. The piperazine compound has a wide application, thus the invention has a certain practical production meaning.

Description

technical field [0001] The invention relates to a piperazine compound, especially a D3 receptor partial agonist for treating central nervous system diseases and a preparation method of an intermediate thereof, belonging to the field of drug synthesis. Background technique [0002] BP897 (1, Scheme 1), chemically named 4-[4-(2-methoxy-phenyl)-piperazinyl]-butyl-2-naphthylcarboxamide, is the first dopamine D3 receptor to enter clinical research body partial agonists. At the end of the last century, a research team jointly formed by the French Institute of Health and Medical Research and the University of Cambridge in the United Kingdom discovered a substance that can suppress drug addiction, bringing hope for human beings to solve the problem of drug addiction physiologically. The substance that can suppress drug addiction is BP897. Pilla et al. (Pilla M, Perachon S, Sautel F, et al. Nature, 1999, 400(6742): 371–375.) studies have shown that BP897 has a good effect in the tr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D295/096C07D295/073C07D295/033C07D239/42C07D487/10C07D295/13
Inventor 徐崇福富利祥郑黄利赵萌萌宋蕴丽
Owner CHANGZHOU UNIV
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