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Synthetic method of hordenine hydrochloride

A technology of hordenine hydrochloride and a synthesis method, which is applied in the field of synthesis of hordenine hydrochloride, can solve the problems of unfavorable industrial production, complex process, high production cost, etc., and achieves convenience for industrial production, simple synthesis process, and high production cost. low cost effect

Inactive Publication Date: 2017-07-04
上海巧坤化工科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] In order to solve the above-mentioned technical problems, the present invention provides a method for synthesizing hordenine hydrochloride, which can solve the problems that most current processes for synthesizing hordenine hydrochloride are relatively complicated, the production cost is high, and it is not conducive to industrial production

Method used

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  • Synthetic method of hordenine hydrochloride
  • Synthetic method of hordenine hydrochloride
  • Synthetic method of hordenine hydrochloride

Examples

Experimental program
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Effect test

example 1

[0031] Amination reaction

[0032] Add 166 g (1 mol, 1 equivalent) of methyl p-hydroxyphenylacetate and 500 ml of methanol successively into the reaction flask, pass through 115 g (2.5 mol, 2.5 equivalents) of dimethylamine, react at 50-60 ° C for 10 hours, and then evaporate the methanol to dryness. Then add 500ml of water to stir for crystallization, cool down to 20-25°C, filter, and dry to obtain 148g of intermediate N,N-dimethyl-p-hydroxyphenylacetamide, with a yield of 82.7%.

example 2

[0034] Amination reaction

[0035] Add 166 g (1 mol, 1 equivalent) of methyl p-hydroxyphenylacetate and 500 ml of methanol successively into the reaction flask, pass through 280 g (6 mol, 6 equivalents) of dimethylamine, react at 50-60°C for 10 hours, evaporate the methanol to dryness, and then Add 500ml of water to stir for crystallization, cool down to 20-25°C, filter, and dry to obtain 146g of intermediate N,N-dimethyl-p-hydroxyphenylacetamide, with a yield of 81.5%.

example 3

[0037] Amination reaction

[0038] Add 166 g (1 mol, 1 equivalent) of methyl p-hydroxyphenylacetate and 500 ml of methanol successively into the reaction flask, pass through 450 g (10 mol, 10 equivalents) of dimethylamine, react at 15-25 ° C for 20 hours, evaporate the methanol to dryness, and then Add 500ml of water to stir for crystallization, cool down to 20-25°C, filter, and dry to obtain 144g of intermediate N,N-dimethyl-p-hydroxyphenylacetamide, with a yield of 80.4%.

[0039] The chemical reaction equation of above-mentioned embodiment 1-3 is:

[0040]

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Abstract

The invention discloses a synthetic method of hordenine hydrochloride. According to the synthetic method of hordenine hydrochloride, methyl 4-hydroxyphenylacetate and dimethylamine are taken as raw materials, a protonic solvent and a polar aprotic solvent are taken as solvents so as to obtain N,N-dimethyl-4-hydroxybenzeneacetamide; N,N-dimethyl-4-hydroxybenzeneacetamide is taken as a raw material, tetrahydrofuran is taken as a solvent, and a reducing agent and a catalyst are added so as to obtain hordenine; hydrochloric acid is added, ethanol is taken as a solvent, and hordenine hydrochloride is obtained via reaction. In the synthetic method, methyl 4-hydroxyphenylacetate is taken as a raw material, hordenine hydrochloride is obtained via two-step synthesis, the raw materials are easily available, the synthesis method is simple, amplification production is convenient to realize, production cost is low, industrialized production is convenient to realize, and market potential is high.

Description

technical field [0001] The invention belongs to the technical field of organic chemical synthesis, and in particular relates to a method for synthesizing hordenine hydrochloride. Background technique [0002] Hordenine can act on adrenaline receptors, and has the effects of relaxing bronchial smooth muscle, constricting blood vessels, vasopressurizing, raising blood pressure and stimulating the central nervous system. It can be used to relieve bronchitis, bronchial asthma, and enhance the tension and movement of the uterus. Protection against radiation damage. [0003] The natural hordenine mainly exists in the root of the leech, the stem of the linden leaf, the heartwood of the false pigeon pea and the stem and leaf of the horn of the king rhinoceros. Separation is relatively difficult, and the product purity is not high. [0004] Hordenine is not conducive to long-term storage, so industrial production produces hordenine hydrochloride, which is convenient for storage and...

Claims

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Application Information

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IPC IPC(8): C07C213/02C07C215/52
CPCC07C213/02C07C231/02
Inventor 左理牟家鹏胡伟杰
Owner 上海巧坤化工科技有限公司
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