Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Method for preparing 4-trifluoromethylphenyl piperazine

A technology of trifluoromethylphenylpiperazine and trifluoromethylphenyl, applied in the field of preparation of 4-trifluoromethylphenylpiperazine, which can solve the problems of high cost of phenyllithium, harsh reaction conditions, high catalyst cost, etc. problems, to achieve the effects of easy control of the reaction, low production risk and high reaction yield

Inactive Publication Date: 2011-05-18
天津均凯农业科技有限公司
View PDF1 Cites 5 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The preparation method of 4-trifluoromethylphenylpiperazine is at present: (1) substituted aniline and diethanolamine carry out cyclization reaction under high temperature condition, and this method raw material is easy to get, easy to operate, but yield is too low; (2) Halogenated benzene is condensed with piperazine under the action of phenyllithium. This method is a normal temperature and pressure reaction with high yield, but the cost of phenyllithium is too high
(3) Substituting N,N-(2-ethanolyl)aniline and ammonia under the catalysis of a catalyst containing copper or cobalt or nickel oxide, condensation under high temperature and high pressure, the catalyst cost required for the reaction is relatively high
(4) Halogenated trifluorotoluene and piperazine react under high temperature and high pressure, and the reaction conditions are relatively harsh

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0019] A preparation method of 4-trifluoromethylphenylpiperazine, which is obtained by neutralizing 4-trifluoromethylphenylpiperazine hydrochloride with alkali, and the alkali used is hydroxide, carbonate, ammonia water , one of triethylamine. Wherein the neutralization reaction temperature ranges from 0°C to 50°C.

[0020] The preparation method of 4-trifluoromethylphenylpiperazine hydrochloride is to use trifluoromethylaniline as raw material, and carry out ring closure reaction with bis(2-chloroethyl)amine under heating conditions.

[0021] The solvent used in the preparation of 4-trifluoromethylphenylpiperazine hydrochloride is one of toluene, n-butanol, diethylene glycol monomethyl ether and xylene.

[0022] The reaction temperature in the preparation of 4-trifluoromethylphenylpiperazine hydrochloride ranges from 110°C to 200°C.

[0023] The above-mentioned bis(2-chloroethyl)amine is prepared by reacting diethanolamine with thionyl chloride under reflux conditions.

[...

Embodiment 1

[0037] Dissolve 2.594 kg of thionyl chloride in 3.6 kg of chloroform, cool to below 0°C in an ice bath, add dropwise 1.33 kg of chloroform solution of 0.86 kg of diethanolamine, gradually rise to room temperature after the dropwise addition, stir for 30 minutes, and heat up to reflux. A large amount of gas is released. After 5 hours of reflux reaction, the temperature was lowered, and solids were gradually precipitated. After cooling down to room temperature, 1.4 kg of bis(2-chloroethyl)amine was obtained by filtration as a white powder, with a yield of 95.8%.

Embodiment 2

[0039] Dissolve 2.594 kg of thionyl chloride in 3 kg of 1,2-dichloroethane, cool the temperature in an ice bath to below 0°C, add 0.86 kg of diethanolamine in 1.1 kg of 1,2-dichloroethane dropwise, and the addition is complete Afterwards, it was gradually raised to room temperature, stirred for 30 minutes, and then heated to reflux, and a large amount of gas was released. After 5 hours of reflux reaction, the temperature was lowered, and solids were gradually precipitated. After cooling down to room temperature, 1.36 kg of bis(2-chloroethyl)amine was obtained by filtration as a white powder, with a yield of 93.2%.

[0040] Part II: Preparation of 4-trifluoromethylphenylpiperazine hydrochloride

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention relates to a method for preparing 4-trifluoromethylphenyl piperazine, which comprises the following steps of: firstly, reacting diethanol amine with thionyl chloride to obtain bis(2-chloroethyl)amine, reacting 4-trifluoromethylaniline with bis(2-chloroethyl)amine in normal butanol or diethylene glycol monomethyl ether under the heating condition to obtain 4-trifluoromethylphenyl piperazine hydrochloride, and neutralizing with an alkaline to obtain the 4-trifluoromethylphenyl piperazine. The method for preparing the 4-trifluoromethylphenyl piperazine has the advantages of high reaction yield, less production of three wastes, easy reaction control, small production danger, simple product purification, high content and the like.

Description

technical field [0001] The invention belongs to intermediates used in the production of medicine and pesticides, in particular to a preparation method of 4-trifluoromethylphenylpiperazine. Background technique [0002] 4-trifluoromethylphenylpiperazine and its hydrochloride, as piperazine compounds, are psychotropic substances with central activity, which can produce excitatory effects similar to amphetamine. The application of N-arylpiperazine is very It is widely used in the synthesis of several categories of drugs, such as antihistamines and antipsychotics. Antidepressants, cough suppressants, etc. [0003] The preparation method of 4-trifluoromethylphenylpiperazine is at present: (1) substituted aniline and diethanolamine carry out cyclization reaction under high temperature condition, and this method raw material is easy to get, easy to operate, but yield is too low; (2) Halogenated benzene is condensed with piperazine under the action of phenyllithium. This method is...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/15C07C209/74C07D295/073
Inventor 尚振华栗晓东张慧丽
Owner 天津均凯农业科技有限公司
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com