Preparation method of N-acetyl-5-methoxytryptamine

A technology of methoxytryptamine and acetic anhydride is applied in the preparation field of synthesizing N-acetyl-5-methoxytryptamine, can solve the problems of slow reaction speed, complicated operation, low yield and the like, and achieves less side reactions, The effect of low dosage and high yield

Inactive Publication Date: 2012-01-25
SHANGHAI CHEM REAGENT RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] The technical problem to be solved by the present invention is to provide a preparation method of N-acetyl-5-methoxytryptamine, using catalyst 4-dimethylaminopyridine, which overcomes the complicated operation, high cost and low yield in the prior art , slow response, etc.

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  • Preparation method of N-acetyl-5-methoxytryptamine
  • Preparation method of N-acetyl-5-methoxytryptamine

Examples

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Embodiment 1

[0025] Add 38.05g (0.2mol) of 5-methoxytryptamine and 200ml of dichloromethane to a reactor equipped with a low-temperature and constant-temperature reaction bath, stirring, and a thermometer respectively. Under stirring, keep the reaction temperature at 5-10°C and drop in 0.5 hours A mixed solution containing 20.4g (0.2mol) of acetic anhydride and dichloromethane solvent (prepared according to the volume ratio of acetic anhydride:dichloromethane=1:2), was added, and 1.2g of 4-DMAP was added, and the reaction was carried out at room temperature for 2 hours.

[0026] Add 200ml of 1mol / L NaOH solution to the reaction solution for neutralization, wash with water to neutrality, add 1.0g of activated carbon to the separated organic phase for decolorization, distill out the dichloromethane solvent under reduced pressure (recycled after recovery), concentrate White crystals precipitated from the solution below 4°C, and after filtration and drying, 43.6 g of the target product N-acetyl...

Embodiment 2

[0028] Add 38.05g (0.2mol) of 5-methoxytryptamine and 300ml of dichloromethane to a reactor equipped with a low-temperature and constant-temperature reaction bath, stirring, and a thermometer respectively. Under stirring, keep the reaction temperature at 5-10°C and drop in 0.5 hours A mixed solution containing 21.44g (0.21mol) of acetic anhydride and dichloromethane solvent (prepared according to the volume ratio of acetic anhydride:dichloromethane=1:3) was added, 2.0g of 4-DMAP was added, and the reaction was carried out at room temperature for 2 hours.

[0029] Add 210ml of 1mol / L NaOH solution to the reaction solution for neutralization, wash with water to neutrality, add 1.8g of activated carbon to the separated organic phase for decolorization, distill out the dichloromethane solvent under reduced pressure (recycled after recovery), concentrated solution White crystals precipitated below 4°C. After filtration and drying, 44.4 g of the target product N-acetyl-5-methoxytrypt...

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Abstract

The invention discloses a preparation method of N-acetyl-5-methoxytryptamine. The preparation method comprises the following steps: adding a raw material, namely 5- methoxytryptamine into a dichloromethane solvent, dripping mixed solution of acetic anhydride and dichloromethane at the dripping time of 0.5-1.0 hour at the temperature of 5-10 DEG C, adding a catalyst, namely 4-DMAP (4-dimethylaminophenol), reacting for 1-2 hours at the normal temperature and collecting a target product from reaction products. Through testing, the product purity is not less than 98%, the yield is not less than 94% and the melting point is 114-117 DEG C. The catalyst, namely the 4-DMAP is adopted for performing N-acylation reaction, the using quantity is low, the speed is fast, the side reactions are few, the reaction conditions are mild, the yield is high, the reaction is performed under normal pressure, the operation is safe, simple and convenient, and the preparation method is suitable for industrial production.

Description

technical field [0001] The invention relates to a preparation method of N-acetyl-5-methoxytryptamine, in particular to a method for synthesizing N-acetyl-5-methoxytryptamine by using catalyst 4-dimethylaminopyridine (4-DMAP) method of preparation. Background technique [0002] N-acetyl-5-methoxytryptamine is also called melatonin, and its English name is Melatonin (MLT). N-acetyl-5-methoxytryptamine is a polypeptide hormone mainly secreted by the pineal gland. Studies have shown that clinically it can regulate biological rhythms, treat insomnia, improve sleep quality, regulate the body's immune function, clear Free radicals in the human body can also prevent the toxic effect of tumor chemotherapy drugs on hematopoietic function, and have broad application prospects in the treatment of various central nervous system diseases. [0003] Its structural formula is as follows: [0004] [0005] In the prior art, Cao Huilan reported a method for preparing N-acetyl-5-methoxytr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/14
Inventor 宋振周艳蒋旭亮詹家荣
Owner SHANGHAI CHEM REAGENT RES INST
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