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Method for preparing N,N-diallyl-5-methoxytryptamine hydrochlorides

A technology of methoxytryptamine hydrochloride and methoxytryptamine, applied in the N field, can solve problems such as long reaction time and environmental pollution, achieve stable product quality, reduce production costs, and be suitable for large-scale continuous production Effect

Active Publication Date: 2012-03-28
SHANGHAI CHEM REAGENT RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The technical problem to be solved by the present invention is to provide a kind of preparation method of N, N-diallyl-5-methoxytryptamine hydrochloride, use organic amine immobilized catalyst, overcome the long reaction time in the prior art, serious environmental pollution

Method used

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  • Method for preparing N,N-diallyl-5-methoxytryptamine hydrochlorides

Examples

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Effect test

Embodiment 1

[0024] The preparation of embodiment 1 organic amine immobilized catalyst

[0025] Add 500ml of anhydrous toluene to a 1000ml three-necked flask equipped with a reflux condenser, stirrer, and thermometer, add 100g of organic amine and 500g of solid-phase silica under stirring at room temperature, and raise the temperature to 110°C within 30 minutes, and keep reflux After reacting for 6 hours, it was cooled down to room temperature, filtered and dried to obtain 589 g of organic amine immobilized catalyst.

Embodiment 2

[0027] Add 209.3g (1.1mol) 5-methoxytryptamine, 600ml N,N-dimethylformamide respectively in a 1000ml three-necked flask with a stirrer and a thermometer, add the organic amine immobilized catalyst prepared in Example 1 63.21g and 160g (2.3mol) of allyl chloride were reacted at room temperature for 8 hours, and the reaction solution was filtered (the filtered catalyst could be put into recycling after being activated by sodium carbonate solution), and the obtained filtrate was evaporated to dryness with 1260ml isopropanol Dissolved, added 92ml of 36wt% hydrochloric acid for hydrochloric acidification, and obtained 270.32g of white crystals of N,N-diallyl-5-methoxytryptamine hydrochloride, with a content of 98.70% and a yield of 88.09%.

Embodiment 3

[0029] Add 209.3g (1.1mol) 5-methoxytryptamine and 800ml N,N-dimethylformamide respectively in a 1000ml three-necked flask with a stirrer and a thermometer, and add the 100g organic amine prepared in Example 1 for immobilization Catalyst and 206.6g (2.7mol) allyl chloride, reacted 6 hours under room temperature, reaction solution was filtered (the catalyst that filters out can be put into recycling after being activated by sodium carbonate solution), after the filtrate obtained is evaporated to dryness, use 1660ml isopropanol Dissolved, added 100ml of 36wt% hydrochloric acid for hydrochloric acidification, and obtained 282.10g of white crystals of N,N-diallyl-5-methoxytryptamine hydrochloride, with a content of 98.86% and a yield of 91.93%.

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Abstract

The invention discloses a method for preparing N,N-diallyl-5-methoxytryptamine hydrochlorides, which is implemented by taking 5-methoxytryptamine as a raw material and taking DMF (dimethyl formamide) as a solvent through the steps of: in the presence of an organic amine immobilized catalyst, carrying out substitution reaction on the catalyst and chloropropene so as to obtain a substitute; and then adding IPA (isopropanol) into the obtained substitute, and carrying out salifying on the obtained product and a hydrochloric acid so as to obtain a target product. Trough detection, the purity of the prepared N,N-diallyl-5-methoxytryptamine hydrochloride is greater than or equal to 98%, and the yield thereof is greater than or equal to 88%. By using the method disclosed by the invention, due to the adoption of the organic amine immobilized catalyst, the reaction process is effectively improved, and the problem that the post-reaction processing is complicated in operation is solved; and meanwhile, the adopted organic amine immobilized catalyst can be recycled after being activated, therefore, the production cost is greatly lowered, the pollution to the environment is reduced, and a prepared product is stable in quality and suitable for large-scale production.

Description

technical field [0001] The invention relates to a preparation method of N,N-diallyl-5-methoxytryptamine hydrochloride, in particular to a method for preparing N,N-diallyl-5-methanol with an organic amine immobilized catalyst Oxytryptamine hydrochloride method. Background technique [0002] N,N-diallyl-5-methoxytryptamine hydrochloride is an important pharmaceutical intermediate with good pharmacological and physiological activities, so it has become an indispensable part in clinical practice and has been widely used . [0003] In the prior art, the method for the synthesis of N, N-diallyl-5-methoxytryptamine hydrochloride mainly takes 5-methoxytryptamine and chloropropene as starting raw materials, and takes place under the action of an inorganic base catalyst. Substitution, followed by salt formation with hydrochloric acid to obtain the target product. [0004] Feng Guangwei, Dai Zeqin, etc. disclosed a simple and efficient method for synthesizing N,N-diallyl-5-methoxytr...

Claims

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Application Information

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IPC IPC(8): C07D209/16
CPCY02P20/584
Inventor 宋振顾慧娟蒋旭亮詹家荣
Owner SHANGHAI CHEM REAGENT RES INST
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