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A kind of preparation method of homopiperazine

A technology of homopiperazine and tosyl homopiperazine, which is applied in the field of medicine, can solve the problems of low purity of the final product, harsh reaction conditions, complicated synthesis process, etc., to suppress the formation of linear by-products and simplify the production process , the effect of improving yield and purity

Active Publication Date: 2017-09-15
渭南畅通药化科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] The purpose of the present invention is to overcome the above-mentioned shortcoming of the prior art, solve the technical problem that the existing synthesis process is complicated, the reaction conditions are harsh, the total yield is low, and the purity of the final product is not high, and it provides a method that can obtain high purity, high The synthetic method of the homopiperazine of yield

Method used

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  • A kind of preparation method of homopiperazine

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Effect test

Embodiment 1

[0031] The method for preparing homopiperazine is as follows:

[0032] (1) The first step: take ethylenediamine and n-butanol and p-toluenesulfonyl chloride to react, then add 50% sodium hydroxide, stir, heat to reflux, then add bromochloropropane and 50% sodium hydroxide solution, and react Centrifuge for 1-3 hours to obtain N,N'-di-p-toluenesulfonyl homopiperazine;

[0033] (2) The second step: sequentially put phenol, hydrobromic acid and N,N'-di-p-toluenesulfonyl homopiperazine into the reaction tank for reaction, concentrate under reduced pressure, remove the remaining phenol and hydrobromic acid, add ethanol , centrifuged to obtain homopiperazine hydrobromide;

[0034] (3) The third step: drop homopiperazine hydrobromide and 50% sodium hydroxide solution into the reaction tank, stir at room temperature, add toluene in the reaction tank, reflux, centrifuge, collect the filtrate, distill under reduced pressure, collect 90 ℃-110℃ or so distillate to obtain homopiperazine....

Embodiment 2

[0036] The method for preparing homopiperazine is as follows:

[0037](1) The first step: put 20-30kg ethylenediamine and 60-80kg n-butanol into the reaction tank, add 140-180kg p-toluenesulfonyl chloride and 70-90kg 50% sodium hydroxide at 25°C, and stir 10-20 minutes, heat to reflux, then add 60-70kg bromochloropropane and 70-90kg 50% sodium hydroxide solution, the pH of the reaction system is 10-12, heat to reflux, react for 1.5-2.5 hours, centrifuge, and dry Get N,N'-di-p-toluenesulfonyl homopiperazine;

[0038] (2) The second step: successively put 60-80kg phenol, 90-110kg hydrobromic acid (content: 45-60%) and 130-150kg N, N'-di-p-toluenesulfonyl homopiperazine into the reaction tank, and reflux React for 4-6 hours, 120°C, concentrate under reduced pressure at 5 mgHg, remove the remaining phenol and hydrobromic acid, then add 40-60 kg of ethanol, stir and crystallize overnight, centrifuge, and dry to obtain homopiperazine hydrobromide;

[0039] (3) The third step: put ...

Embodiment 3

[0041] The method for preparing homopiperazine is as follows:

[0042] (1) The first step: Get 25kg of ethylenediamine and 75kg of n-butanol and put it into a 500L enamel reaction tank. At 25°C, add 160kg of p-toluenesulfonyl chloride and 80kg of 50% sodium hydroxide, stir for 15 minutes, and heat to reflux , then add 65kg bromochloropropane and 80kg 50% sodium hydroxide solution, the pH of the reaction system is 12, heat to reflux, react for 2 hours, centrifuge, and dry to obtain 143kg of N,N'-di-p-toluenesulfonyl homopiperazine , yield 91.1%, content 99.1%;

[0043] (2) The second step: put 70kg of phenol, 100kg of hydrobromic acid (content: 60%) and 140kg of N,N'-di-p-toluenesulfonyl homopiperazine into a 500L enamel reaction tank in sequence, and reflux for 5h at 120°C , concentrated under reduced pressure at 5 mgHg, removed remaining phenol and hydrobromic acid, then added 50kg of ethanol, stirred and crystallized overnight, centrifuged, dried to obtain 78.7kg homopipera...

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Abstract

The invention discloses a preparation method of homopiperzine. The preparation method comprises the following steps: by taking ethylene diamine as a raw material, performing acylation reaction on ethylene diamine and toluenesulfonyl chloride in an n-butyl alcohol solvent to prepare N, N'-dipara-toluene sulfonyl ethylene diamine; directly performing ring-closure reaction on N, N'-dipara-toluene sulfonyl ethylene diamine which does not need to be separated from a reaction liquid and chlorobromide under the action of sodium hydroxide to prepare N, N'-dipara-toluene sulfonyl homopiperzine; removing sulfonyl under the action of hydrobromic acid and phenol to obtain homopiperzine hydrobromide; finally, dissociating with sodium hydroxide and bringing water from toluene to obtain high-purity homopiperzine. The production method is simple to operate, cost-saving, convenient for large-scale production, and can be preparing high-purity high-yield homopiperzine.

Description

Technical field [0001] The invention belongs to the field of medical technology, relates to a widely used intermediate preparation method, and specifically relates to a new process for synthesizing homopiperazine. Background technique [0002] Homopiperazine can not only be widely used in the field of fine chemicals, such as antioxidants, foaming agents, cosmetic emulsifiers, high-energy density materials, etc., but it is also an important drug synthesis intermediate. By modifying its structure And transformation, it has good curative effect in allergies, inflammation, mental illness and other diseases, and is mainly used in the production of fasudil hydrochloride, homopiperazine hydrochloride, cyclizine, carbamazepine, quinolones and chlorcyclizine. Therefore, the market demand for homopiperazine is huge and it has good application prospects. [0003] In 1961, Poppeludorf et al. reported that N-(2-cyanoethyl)ethylenediamine was used as raw material and Gerdler G-49A as cat...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D243/08
CPCC07D243/08
Inventor 畅水平
Owner 渭南畅通药化科技有限公司
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