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Method for preparing N-methyl-5-hydroxytryptamine by taking 5-hydroxytryptamine hydrochloride as raw material

A technology of serotonin hydrochloride and serotonin, which is applied in organic chemistry and other fields, and can solve the problems of complex components and low content of active ingredients of N-methyl-5-serotonin

Inactive Publication Date: 2021-02-02
BLRH BIOTECH CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In order to solve the above-mentioned technical problems, the present invention provides a method for preparing N-methyl-5-hydroxytryptamine using 5-hydroxytryptamine hydrochloride as a raw material, using 5-hydroxytryptamine hydrochloride as a raw material, through primary amine formylation and reduction Hydrogenation to obtain high-purity N-methyl-5-hydroxytryptamine compounds, changing the current situation of low active ingredient content and complex components of N-methyl-5-hydroxytryptamine in biological extraction methods

Method used

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  • Method for preparing N-methyl-5-hydroxytryptamine by taking 5-hydroxytryptamine hydrochloride as raw material
  • Method for preparing N-methyl-5-hydroxytryptamine by taking 5-hydroxytryptamine hydrochloride as raw material
  • Method for preparing N-methyl-5-hydroxytryptamine by taking 5-hydroxytryptamine hydrochloride as raw material

Examples

Experimental program
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Effect test

Embodiment 1

[0031] Add 716ml of DMF solvent into a 2L three-necked flask, add 21.26g (0.100mol) of 5-hydroxytryptamine hydrochloride under stirring, and then add 20.14ml (0.250mol) of pyridine into the three-necked flask, keep the temperature at 25°C, and stir for 20min. Then put the three-necked flask into an ice-water bath, cool the reaction solution to 10°C, and then add 9.7g of formic acetic anhydride solution (0.110mol) dropwise to the three-necked flask, the dropping process controls the reaction temperature within 12-15°C, The time is 20 minutes. After the dropwise addition, keep at 12-15°C to continue the reaction for 2h.

[0032] Then add 477mL of deionized water under stirring, then add 286ml of dichloromethane, stir for 10min and then let stand for 5min, separate the organic phase of the lower layer of dichloromethane, then add 286ml of dichloromethane, stir for 10min and let stand for 5min, separate For the organic phase of dichloromethane in the lower layer, repeat this extr...

Embodiment 2

[0037] Add 830ml of DMF solvent into a 2L three-necked flask, add 21.26g (0.100mol) of 5-hydroxytryptamine hydrochloride under stirring, and then add 28.19ml (0.350mol) of pyridine into the three-necked flask, keep the temperature at 20°C, and stir for 10min. Then put the three-necked flask into an ice-water bath, cool the reaction solution to 10°C, and then add 11.44g of formic acetic anhydride solution (0.130mol) dropwise to the three-necked flask, and control the reaction temperature within 10-13°C during the dropping process. The time is 30 minutes. After the dropwise addition, keep at 10-13°C to continue the reaction for 1.5h.

[0038] Then add 550mL of deionized water under stirring, then add 330ml of dichloromethane, stir for 10min and let it stand for 5min, separate the lower layer of dichloromethane organic phase, then add 330ml of dichloromethane, stir for 10min and let stand for 5min, separate the lower layer of dichloromethane Chloromethane organic phase, repeat t...

Embodiment 3

[0043] Add 780ml of DMF solvent into a 2L three-necked flask, add 21.26g (0.100mol) of 5-hydroxytryptamine hydrochloride under stirring, and then add 24.16ml (0.300mol) of pyridine into the three-necked flask, keep the temperature at 20°C, and stir for 10min. Then put the three-necked flask into an ice-water bath, cool the reaction solution to 10°C, and then add 10.56g of formic acetic anhydride solution (0.120mol) dropwise to the three-necked flask, and control the reaction temperature within 12-14°C during the dropping process. The time is 30 minutes. After the dropwise addition, keep at 12-14°C to continue the reaction for 2h.

[0044] Then add 520ml of deionized water under stirring, then add 312ml of dichloromethane, stir for 10min and then let it stand for 5min, separate the organic phase of the lower layer of dichloromethane, then add 312ml of dichloromethane, stir for 10min and then let it stand for 5min, separate For the organic phase of dichloromethane in the lower ...

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Abstract

The invention discloses a method for preparing N-methyl-5-hydroxytryptamine by taking 5-hydroxytryptamine hydrochloride as raw material. The method comprises the steps of firstly, carrying out formylation reaction on acetic formic anhydride and 5-hydroxytryptamine hydrochloride to generate a monoformylation product of primary amine; and reducing by lithium aluminum hydride to obtain the N-methyl-5-hydroxytryptamine. According to the method, 5-hydroxytryptamine hydrochloride is used as a raw material, the generation of N,N-dimethyl 5-hydroxytryptamine which is a dimethylation product is inhibited through primary amine formylation and reductive hydrogenation, and compared with a mixture containing N-methyl-5-hydroxytryptamine obtained through a biological extraction method, the method has the advantages in product purity, the N-methyl-5-hydroxytryptamine with relatively high single purity can be provided for medical research, the influence of other components in the extract on a researchresult is eliminated, and the current situations of low content of effective components and complex components of the N-methyl-5-hydroxytryptamine in a biological extraction method are changed.

Description

technical field [0001] The invention relates to the preparation of N-methyl-5-hydroxytryptamine, in particular to a method for preparing N-methyl-5-hydroxytryptamine by using 5-hydroxytryptamine hydrochloride as a raw material. Background technique [0002] Toad Su, a traditional Chinese medicine, is the dry secretion of the posterior ear glands and skin glands of the bufo family Bufo (or black-orbited toad). Chansu Injection has been used clinically at present. Chansu Injection is extracted from the skin glands and post-auricular gland secretions of bufo animals using advanced scientific technology, and is refined from physiologically active water-soluble indole base derivatives. Chansu Injection clears heat and detoxifies, and is used for acute and chronic suppurative infections; it can also be used as an adjuvant anti-tumor drug. In order to analyze the chemical composition of Chansu Injection, some scholars have studied the chemical composition of the water-soluble part...

Claims

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Application Information

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IPC IPC(8): C07D209/16
CPCC07D209/16
Inventor 赵云现李迁田俊波邢瑞静贾博硕赵凯
Owner BLRH BIOTECH CO
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