Method for synthesizing 1, 8-diazabicycle

A diazabicyclo and synthesis method technology, applied in the field of 1,8-diazabicyclo synthesis, capable of solving problems such as low yield and harsh reaction conditions

Inactive Publication Date: 2019-05-24
淄博鸿润新材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The present invention aims at the technical defects of the prior art, and provides a synthesis method of 1,8-diazabicyclo, so as

Method used

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  • Method for synthesizing 1, 8-diazabicycle

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Embodiment 1

[0015] A kind of synthetic method of 1,8-diazabicyclo, with epsilon caprolactam as starting material, first react with hydroquinone in the presence of acrylonitrile, then pass dry Hydrogen chloride gas until the solution is saturated, continue to react under ice bath for more than 10 hours, suction filter under nitrogen protection, add benzyl chloride to react; mix the reaction product with sodium perborate, and then dissolve in dichloromethane in the presence of ethylenediaminetetraacetic acid Reflux for 8 hours; then add 3-tert-butyl salicylaldehyde, add 3-phenylpropionic acid at 45°C under stirring conditions, keep the temperature constant until the raw materials disappear completely, cool down to room temperature, add water to dilute 3 times, and then Add 4-nitrobenzyl chloride to stir the reaction, filter to obtain a solid, and then extract the filtrate with ethyl acetate three times, collect the solid phase, dry with anhydrous magnesium sulfate, and dry under reduced pres...

Embodiment 2

[0017] A kind of synthetic method of 1,8-diazabicyclo, with epsilon caprolactam as starting material, first react with hydroquinone in the presence of acrylonitrile, then pass dry Hydrogen chloride gas until the solution is saturated, continue to react under ice bath for more than 10 hours, suction filter under nitrogen protection, add benzyl chloride to react; mix the reaction product with sodium perborate, and then dissolve in dichloromethane in the presence of ethylenediaminetetraacetic acid Reflux for 8 hours; then add 3-tert-butyl salicylaldehyde, add 3-phenylpropionic acid at 45°C under stirring conditions, keep the temperature constant until the raw materials disappear completely, cool down to room temperature, add water to dilute 3 times, and then Add 4-nitrobenzyl chloride to stir the reaction, filter to obtain a solid, and then extract the filtrate with ethyl acetate three times, collect the solid phase, dry with anhydrous magnesium sulfate, and dry under reduced pres...

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Abstract

The invention provides a synthesis method of 1, 8-diazabicycle. According to the technical scheme, a synthesis route of DBU is innovatively designed. Specifically, the method comprises the steps of firstly, reacting epsilon caprolactam, acrylonitrile and hydroquinone to generate N-(beta-cyanoethyl)-epsilon caprolactam, on the basis, reacting the N-(beta-cyanoethyl)-epsilon caprolactam with p-toluenesulfonic acid under a catalytic condition, then carrying out ice bath, reacting the N-(beta-cyanoethyl)-epsilon caprolactam with benzyl chloride under the protection of nitrogen, reacting the obtained product with sodium perborate by taking EDTA as a catalyst, and mixing a reaction product with 3-phenylpropionic acid and then reacting the mixture with 4-nitrochlorobenzyl to obtain the product; filtering the reaction product, extracting the filtrate with ethyl acetate after filtering, performing solid-liquid separation, merging solid phases, and drying the solid phases under reduced pressureto obtain the final product. According to the method, a brand-new synthetic route is adopted, the reaction condition is mild, the cost of raw materials is low, and the method has quite high popularization prospect.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a synthesis method of 1,8-diazabicyclo. Background technique [0002] 1,8-Diazabicyclo(5,4,0)-7-undecene (DBU) is mainly used as a catalyst for the production of polyurethane and other chemicals, such as ammonia and dichloroethane in its In the presence of the reaction to generate piperazine, it is an excellent dehydrating agent, epoxy resin hardener, antirust agent, and can also be prepared as a high-grade corrosion inhibitor. Currently widely used in the production of cephalosporin semi-synthetic antibiotics. Also used in organic synthesis reactions and semi-synthetic antibiotics. Catalyst for the production of polyurethane and other chemical products, such as the reaction of ammonia and dichloroethane to generate piperazine in its presence, is an excellent dehydrating agent, epoxy resin hardener, rust inhibitor, can Formulated advanced corrosion inhibitors. Wide...

Claims

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Application Information

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IPC IPC(8): C07D487/04
Inventor 甄美静高希会李丽刘清学张俊红耿世淑吴小峰李强英郑开军李培成
Owner 淄博鸿润新材料有限公司
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