Process for producing hydrochloric berberine

A technology of berberine hydrochloride and dimethoxyphenylacetate is applied in the field of preparation of broad-spectrum antibiotic berberine hydrochloride, which can solve the problems of inconvenient operation and high cost

Active Publication Date: 2008-08-20
CHANGZHOU YABANG PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Northeast Pharmaceutical General Factory also reported the same route (ZL 01106089.1), but the process used a copper catalyst during the ring formation process, resulting in the need for decopper treatment after the reaction, which is inconvenient to operate and high in cost

Method used

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  • Process for producing hydrochloric berberine
  • Process for producing hydrochloric berberine
  • Process for producing hydrochloric berberine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Embodiment 1: the preparation of 1-(methoxymethyl)-2,3-dimethoxybenzene (II)

[0020] 168 grams of 2,3-dimethoxybenzyl alcohol (I) was dissolved in 350 mL of dichloromethane, 150 mL of 30% aqueous sodium hydroxide solution was added, and 138 grams of dimethyl sulfate was added dropwise at 80°C. After the dropwise addition, continue to stir the reaction at 80° C. until the raw material point disappears. The water phase was separated, and the organic phase was washed with 150 mL of water and 150 mL of 10% hydrochloric acid respectively. After drying, the solvent was evaporated to obtain 178 grams of oily 1-(methoxymethyl)-2,3-dimethoxybenzene , yield 98%. The oily product was directly used in the next reaction.

Embodiment 2

[0021] Embodiment 2: the preparation of 2-(methoxymethyl)-3,4-dimethoxybenzyl chloride (III)

[0022] 182 g of 1-(methoxymethyl)-2,3-dimethoxybenzene (II) was dissolved in 400 mL of toluene, and 200 mL of hydrochloric acid solution in which 33 g of paraformaldehyde was dissolved was added dropwise at 30°C. After the dropwise addition, keep the solution at 30°C, and continue to stir the reaction until the raw material point disappears. The water phase was separated, and the organic phase was washed with 150 mL of water and 150 mL of saturated sodium bicarbonate solution respectively. After drying, the solvent was evaporated to obtain oily 2-(methoxymethyl)-3,4-dimethoxychloride 210 grams of benzyl, yield 91%. The oily product was directly used in the next reaction.

Embodiment 3

[0023] Embodiment 3: the preparation of 2-(methoxymethyl)-3,4-dimethoxyphenylacetonitrile (IV)

[0024] 230 grams of 2-(methoxymethyl)-3,4-dimethoxybenzyl chloride (III) was dissolved in 500 mL of toluene, 200 mL of water and 75 grams of sodium cyanide were added, and 32 grams of tetrabutyl ammonium bromide. At 100 °C, the reaction was stirred until the starting point disappeared. The water phase was separated, and the organic phase was washed with 150 mL of water and 150 mL of saturated sodium bicarbonate solution, dried, and evaporated to dryness, and the crude product obtained was recrystallized with ethanol to obtain 2-(methoxymethyl)-3,4-bis 210 g of methoxyphenylacetonitrile, melting point 52-54°C, yield 95%.

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Abstract

The invention relates to a preparation method of berberine hydrochloride which is a broad spectrum antibiotic. The method takes 2, 3-dimethoxy benzyl alcohol and homopiperony lamine as raw materials to prepare the berberine hydrochloride by six steps of reaction, namely, alkylation, chloromethylation, cyanidation, alcoholysis, condensation and cyclization. The synthetic technology has easily available materials, high yield but low cost, thus being suitable for industrial production.

Description

technical field [0001] The invention relates to a preparation method of a medicinal raw material drug, in particular to a preparation method of a broad-spectrum antibiotic berberine hydrochloride. Background technique [0002] Berberine hydrochloride, also known as berberine hydrochloride, is a clinically widely used antibacterial drug. Berberine hydrochloride has a broad antibacterial spectrum and has inhibitory effects on a variety of Gram-positive and negative bacteria, including Shigella, pneumococcus, Staphylococcus aureus, streptococcus, typhoid bacillus, diphtheria bacillus, Vibrio cholerae, Neisseria meningitidis, Shigella, etc. have a strong inhibitory effect, and also have a certain effect on amoeba. Clinically, it is mainly used for Shigella bacillus and other intestinal infections. Berberine can be extracted from plants such as Coptis chinensis, but due to the limitation of plant resources, the research work of chemical total synthesis of berberine has high eco...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D455/03
Inventor 陈再新陶锋夏正君马绍明
Owner CHANGZHOU YABANG PHARMA
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