Preparation method for green synthesis of N-acetyl-5-methoxytryptamine

A methoxytryptamine and green synthesis technology, which is applied in the preparation of organic compounds, carboxylic acid nitrile preparation, chemical instruments and methods, etc., can solve the problems of high energy consumption and high product loss, and achieve simplified processes, improved yields, Realize the effect of green synthesis

Inactive Publication Date: 2021-06-08
TECHNO (FUJIAN) FOOD INGREDIENTS CO LTD +1
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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 overcome the deficiency of prior art, provide a kind of preparation method of green synthetic N-acetyl-5-methoxytryptamine, in solving 2-cyanoethyl malonate diethyl ester needs to pass high temperature and high vacuum The way of distillation and the problems of high energy consumption and high product loss caused by the separation of by-products provide a safe and environmentally friendly reaction process, thereby effectively realizing green synthesis and better adapting to the actual needs of industrial production and development

Method used

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  • Preparation method for green synthesis of N-acetyl-5-methoxytryptamine
  • Preparation method for green synthesis of N-acetyl-5-methoxytryptamine
  • Preparation method for green synthesis of N-acetyl-5-methoxytryptamine

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Embodiment 1

[0041] The present embodiment is a green preparation method for synthesizing N-acetyl-5-methoxytryptamine, the steps of which are as follows:

[0042] (1) Addition reaction

[0043]At 20°C, slowly add 15g of the basic catalyst sodium methoxide into 600g of diethyl malonate, and dropwise add 198g of acrylonitrile, and stir the reaction at 60°C for 3 hours. 30% sulfuric acid to neutralize to a pH value of 7, and then add 1600ml of water according to the volume ratio of the reaction solution: water = 1:2 for extraction; after extraction, the reaction solution is dehydrated by adding a dehydrating agent, anhydrous sodium sulfate, to a moisture content of 0.12% And obtain 800ml intermediate 1 reaction solution; Dehydrating agent is applied mechanically after drying, and waste water goes to biochemical system to process;

[0044] (2) Hydrogenation reaction

[0045] Transfer the above-mentioned 800ml intermediate 1 reaction liquid into the hydrogenation kettle, add 2400ml solvent m...

Embodiment 2

[0057] The present embodiment is a green preparation method for synthesizing N-acetyl-5-methoxytryptamine, the steps of which are as follows:

[0058] (1) Addition reaction

[0059] Slowly add 20g of basic catalyst sodium hydroxide at 30°C to 600g of diethyl malonate, and dropwise add 198g of acrylonitrile, and stir the reaction at 50°C for 2 hours. After the reaction is completed, add Acetic acid was neutralized to a pH value of 7, and then extracted three times according to the volume ratio of the reaction solution: water = 1:3 plus 2400ml of water; after extraction, the reaction solution was dehydrated by adding a dehydrating agent anhydrous magnesium sulfate until the water content was 0.1% to obtain 790ml of intermediate Body 1 reaction solution; the dehydrating agent is dried and applied mechanically, and the waste water is processed in the biochemical system;

[0060] (2) Hydrogenation reaction

[0061] Transfer the above-mentioned 790ml intermediate 1 reaction liquid...

Embodiment 3

[0073] The present embodiment is a green preparation method for synthesizing N-acetyl-5-methoxytryptamine, the steps of which are as follows:

[0074] (1) Addition reaction

[0075] At 30°C, slowly add 13g of basic catalyst triethylamine into 600g of diethyl malonate, and dropwise add 198g of acrylonitrile, and stir the reaction at 55°C for 3 hours. After the reaction is completed, add The concentration is 15% hydrochloric acid to neutralize to a pH value of 7, and then extract five times according to the volume ratio of the reaction solution: water = 1:5 plus 4000ml of water; after extraction, the reaction solution is dehydrated to water by adding a dehydrating agent anhydrous calcium chloride 0.15% to obtain 785ml intermediate 1 reaction solution; the dehydrating agent is dried and applied mechanically, and the waste water is removed to the biochemical system for treatment;

[0076] (2) Hydrogenation reaction

[0077] Transfer the above-mentioned 785ml intermediate 1 react...

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Abstract

The invention discloses a preparation method for green synthesis of N-acetyl-5-methoxytryptamine. Diethyl malonate and acrylonitrile are used as initial raw materials, and the product N-acetyl-5-methoxytryptamine is obtained through addition, hydrogenation, coupling, cyclization, ring opening, decarboxylation and acylation reaction processes. According to the addition reaction, impurities in a reaction system are removed by adopting a water extraction mode, so that the problems of high energy consumption, high product loss and the like caused by separating an intermediate by adopting a high-temperature and high-vacuum distillation mode in the prior art are avoided; and in the processes of coupling reaction, cyclization reaction, ring-opening reaction, decarboxylation reaction and acylation reaction, water is used as a reaction solvent, the reaction process is safe and environment-friendly, green synthesis is effectively realized, and the method is suitable for industrial actual production.

Description

technical field [0001] The invention relates to the technical field of synthesis of pharmaceutical raw material intermediates, in particular to a preparation method of N-acetyl-5-methoxytryptamine. Background technique [0002] N-acetyl-5-methoxytryptamine, also known as melatonin, belongs to indole heterocyclic compounds and is one of the hormones secreted by the pineal gland of the brain. Its well-known functions are mainly to improve sleep (dosage 0.1-0.3mg), shorten the time of awakening and falling asleep before going to bed, improve sleep quality, significantly reduce the number of awakenings during sleep, shorten the stage of light sleep, prolong the stage of deep sleep, and The morning wake-up threshold decreases, and it has a strong function of adjusting jet lag. In recent years, in the US market, melatonin products have developed into mainstream best-selling varieties in health food. my country began to produce melatonin in the mid-1990s, and now it has been able...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/16C07C253/30C07C253/34C07D471/04C07D209/42C07C255/19
CPCC07D209/16C07C253/30C07C253/34C07D471/04C07D209/42C07C255/19
Inventor 罗华东陈子昂陈建明刘委座邱语康陈爱琴周健李安冰蓝姗姗
Owner TECHNO (FUJIAN) FOOD INGREDIENTS CO LTD
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