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Process for preparing N-methyl homopiperazine from 2-haloethylamine compound

A technology of methylhomopiperazine and haloethylamine, which is applied in the field of preparing N-methylhomopiperazine, can solve the problems of unstable yield, violent heat release, and many wastes, and achieve high production operation safety, The effect of simple synthesis process and convenient reaction operation

Inactive Publication Date: 2017-11-24
SUZHOU BAILINGWEI HYPERFINE MATERIAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This method has two very obvious disadvantages: the first is that lithium aluminum hydride needs to be used for reduction, the heat release is violent, the danger is very high, and the generated aluminum salt waste residue is also particularly large; the second is the repeatability of the entire route. Relatively poor, the yield is extremely unstable in the actual production process
[0006] In view of the above-mentioned technology for preparing N-methylhomopiperazine, there are many three wastes, the risk of reducing reagents is relatively large, and the operation safety is poor.

Method used

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  • Process for preparing N-methyl homopiperazine from 2-haloethylamine compound
  • Process for preparing N-methyl homopiperazine from 2-haloethylamine compound
  • Process for preparing N-methyl homopiperazine from 2-haloethylamine compound

Examples

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example 1

[0077] The method for preparing homopiperazine described in this example may further comprise the steps:

[0078] Step 1: Preparation of N-(2-chloroethyl)trifluoroacetamide

[0079]

[0080] Under stirring at room temperature, add 30L of ethanol, 3.48kg of 2-chloroethylamine hydrochloride and 4.27kg of ethyl trifluoroacetate to the 50L reaction kettle in sequence, stir well, cool to 0°C, and dropwise add 3.04kg of triethylamine , 2 hours to drop. After dripping, react at room temperature for 4 hours, and the reaction ends.

[0081] Ethanol was recovered by distillation under reduced pressure, and the residue was beaten and washed with 10 L of tap water. Filtrate, drain the filter cake, and dry in an oven at 50°C for 4 hours to obtain 4.92Kg of a white low-melting solid product with a yield of 93.4% and a melting point of 59-60°C.

[0082] Step 2: Preparation of N-methyl-N'-trifluoroacetylethylenediamine

[0083]

[0084] Under stirring at room temperature, 25L of ace...

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Abstract

The invention discloses a process for preparing N-methyl homopiperazine from 2-haloethylamine compound, and the process comprises the following steps: Step 1, taking the 2-halogenated ethylamine compound as a raw materia to react with ethyl trifluoroacetate to obtain N-(2-Haloethyl) trifluoroacetamide; Step (2) taking the N-(2-Haloethyl) trifluoroacetamide as a raw material to react with methylamine or methylamine hydrochloride to obtain N-methyl-N'-trifluoroacetyl ethylenediamine; Step (3) taking the N-methyl-N'-trifluoroacetyl ethylenediamine as a raw material to react with 1,3-disubstituted propane compound to obtain N-methyl-N'-trifluoroacetyl homopiperazine; Step (4) taking the N-methyl-N'-trifluoroacetyl homopiperazine as a raw material to react with a hydrogen chloride ethanol solution to obtain N-methyl homopiperazine dihydrochloride; and Step (5) taking the N-methyl homopiperazine dihydrochloride as a raw material to prepare the N-methyl homopiperazine by alkalization. The process has the advantages of simple operation, low cost, high yield, low pollution and suitability for industrialized production.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a process for preparing N-methylhomopiperazine by utilizing 2-halogenated ethylamine compounds. Background technique [0002] N-methylhomopiperazine is an aza seven-membered ring compound and an important pharmaceutical intermediate. Most of its derivatives have strong biological activity and medicinal value. According to the query results on Reaxys, there are currently 193 international patents using N-methylhomopiperazine to develop various new drugs such as antibacterial drugs and cardiovascular drugs, and its application prospects are very promising. [0003] At present, the mature method for preparing N-methylhomopiperazine in large quantities currently only has the following synthetic route: [0004] Using N-methyl-4-piperidone as a raw material, it is condensed with hydroxylamine hydrochloride first, then rearranged by Beckmann, and finally reduced ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D243/08
CPCC07D243/08
Inventor 龙韬习文兵邹增龙
Owner SUZHOU BAILINGWEI HYPERFINE MATERIAL
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