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Hordenine synthesis method

A synthetic method and technology of barley base, which is applied in the field of chemical synthesis of natural product barley base, can solve the problems of low quality, excessive formaldehyde residue, and yellowish color of the product, and achieve simple operation, easy-to-obtain raw materials, and cheap and easy-to-obtain raw materials Effect

Inactive Publication Date: 2014-01-01
SHAANXI JIAHE PHYTOCHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This route is one-step reaction to obtain the product, the route is relatively simple, but the price of raw material tyramine is high, and because a large amount of formaldehyde is used, the residual formaldehyde in the product exceeds the standard, the final product is yellowish in color, and the quality is not high

Method used

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preparation example Construction

[0020] Firstly, the intermediate 4-bromoethylphenol is prepared: the raw material p-hydroxyphenethyl alcohol and 48% HBr are fed according to the feeding amount (g:ml) 1: (5-10) to prepare the intermediate 4-bromoethylphenol. The reaction temperature range is 50-100° C., and the reaction time is 10-28 hours.

[0021] Then carry out the synthesis of barley base: the intermediate 4-bromoethylphenol, the dimethylamine methanol solution with a content greater than 45% is fed according to (g:ml) 1: (3~15), or the 4-bromoethylphenol Add dimethylamine gas into the methanol solution to prepare the product barleyine. The reaction temperature range is 20-50° C., and the reaction time is 4-24 hours.

[0022]

[0023] In the present invention, the preparation of the intermediate 4-bromoethylphenol adopts cheap and easy-to-purchase p-hydroxyphenethyl alcohol as raw material for selective bromination. In the bromination method, bromination can be carried out with bromine under the cond...

Embodiment 1

[0026] 1] Preparation of 4-bromoethylphenol

[0027] Take 50g of p-hydroxyphenylethanol, dissolve it in 250ml HBr solution with a concentration of 48%, raise the temperature to 80°C, stir for 16h, cool to room temperature, filter, wash with water until neutral, and dry to obtain 72g of white solid.

[0028] 2] Preparation of hordeline

[0029] Take 20g of 4-bromoethylphenol prepared in step 1, 100ml of 45% dimethylamine methanol solution, stir and react at room temperature for about 18h, stop the reaction after TLC detects that the reaction is complete, filter, and recycle the filtrate to dryness under reduced pressure to obtain The light yellow solid was refined with ethanol water to obtain 19.2 g of pure barleyine.

Embodiment 2

[0031] 1] Preparation of 4-bromoethylphenol

[0032] Take 50g of p-hydroxyphenylethanol, dissolve it in 286ml HBr solution with a concentration of 48%, raise the temperature to 75°C, stir for 24h, cool to room temperature, filter, wash with water until neutral, and dry to obtain 73.5g of white solid.

[0033] 2] Preparation of hordeline

[0034] Take 20 g of 4-bromoethylphenol prepared in step 1 and dissolve in 100 ml of anhydrous methanol, feed dimethylamine gas to saturation at normal temperature, stop ventilation, stir for 8 h, stop the reaction after TLC detects that the reaction is complete, filter, and the filtrate reduces The solvent was recovered under pressure to dryness to obtain a light yellow solid, which was purified with ethanol and water to obtain 18.4 g of pure product.

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Abstract

The invention provides a hordenine synthesis method. The method is short in route, low in cost, high in yield, simple in operation and applicable to industrial production, raw materials are easy to get, and an obtained product is qualified. According to the method, 4-Hydroxyphenethyl alcohol is used as the raw materials and condensed with dimethylamine through chloro, and the qualified product-hordenine is obtained by two-step reaction with high yields. The hordenine synthesis method only includes the following steps: first, preparing 4-bromomethyl phenol, and second obtaining the hordenine through synthesis.

Description

technical field [0001] The invention belongs to the field of organic chemistry and relates to a chemical synthesis method of natural product barleyine. Background technique [0002] Hordenine, also known as hordenine, chemically named 4-(2-dimethylaminoethyl)phenol, pharmacological models show that it can act on adrenergic receptors, and has the functions of relaxing bronchial smooth muscle, constricting blood vessels, and increasing blood vessels. It can be used to relieve bronchitis, bronchial asthma, and enhance the tension and movement of the uterus. It has a protective effect on radiation damage. [0003] [0004] Hordeline mainly exists in the root of Desmodium gangeticum (L.) DC.; the stem of D.tiliaefolium G.Don; the false pigeon pea (D.cephalotes Wall. The heart of )d; the root and stem of wood spiral acacia (Acacia spirorbis Labill); the stem of camel thorn (Alhagi pseudodalhagi (Bieb.) Desv.); .R.)L.Benson.), whole plant C.ramillosa Cutak., Obregonia denegrii...

Claims

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Application Information

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IPC IPC(8): C07C215/50C07C213/04
Inventor 肖金霞郭文华王春德
Owner SHAANXI JIAHE PHYTOCHEM
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