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Synthetic process of berberine

A synthesis process, a technology for berberine, applied in the direction of organic chemistry, etc., can solve the problems of difficult process, high cost, low yield, etc., and achieve the effects of avoiding cyanidation reaction, reducing toxicity, and reducing cost

Inactive Publication Date: 2017-03-29
佑华制药(乐山)有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The object of the present invention is a berberine synthesis process, which solves the problems of high cost, high process difficulty, low yield and high toxicity of the original berberine synthesis process

Method used

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  • Synthetic process of berberine

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Embodiment

[0029] a. First, use catechol and dichloromethane as raw materials, under NaOH condition, dimethyl sulfoxide as solvent, and synthesize piperonyl ring at 95-120°C;

[0030] b. Peperonyl and dimethylformamide in POCl 3 Formylation occurs under conditions to synthesize piperonal;

[0031] c, piperonal and nitromethane undergo Henry reaction nitration under the conditions of sodium acetate, 95% ethanol and methylamine hydrochloride to generate β-nitro-3,4-dioxymethene styrene;

[0032] d, β-nitro-3,4-dioxymethene styrene is reduced to piperonyl ethylamine by zinc amalgam in 95% ethanol solution;

[0033] e, piperethylamine and 2,3-dimethoxybenzaldehyde in Raney nickel, H 2 Condensation hydrogenation under conditions to generate N-2,3-dimethoxybenzyl piperonyl ethylamine hydrochloride or piperonyl ethylamine and 2,3-dimethoxybenzaldehyde under the conditions of Pd / C ammonium formate and formic acid at 45- React at 60°C to generate N-2,3-dimethoxybenzylpiperethylamine hydrochlor...

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Abstract

The invention discloses a synthetic process of berberine. The synthetic process comprises the following synthetic route: pyrocatechol and dichloromethane are taken as raw materials and dimethyl sulphoxide is taken as a solvent to synthesize 1,3-benzodioxole; 1,3-benzodioxole is subjected to ViLsmeiar formylation to synthesize heliotropin; heliotropin undergoes nitration through a Henry reaction to generate beta-nitro-3,4-dioxomethenyl styrene; beta-nitro-3,4-dioxomethenyl styrene is subjected to Clemmensen reduction to generate 3,4-(methylenedioxyphenyl)ethylamine; and 3,4-(methylenedioxyphenyl)ethylamine and 2,3-dimethoxy benzaldehyde condense, and the obtained product is reduced to generate N-2,3-dimethoxybenzyl [3,4-(methylenedioxy)phenyl]ethylamine hydrochloride. N-2,3-dimethoxybenzyl [3,4-(methylenedioxy)phenyl]ethylamine hydrochloride is cyclized in a condition of glyoxal, formic acid and copper sulphate to generate berberine hydrochloride. According to the synthetic route, cyanation is avoided and toxicity is reduced. Zinc amalgam is adopted to replace H2Ni and LiAlH4, so that the cost is greatly reduced, the process difficulty is reduced, and the product yield is increased.

Description

technical field [0001] The invention belongs to the field of organic synthesis of medicines, and in particular relates to a synthesis process of berberine. Background technique [0002] Berberine is an important alkaloid, which has been used in traditional Chinese medicine for a long time in our country. It can be extracted from plants such as Coptis chinensis, Cortex Phellodendri, and three needles. It has a significant antibacterial effect. The commonly used berberine hydrochloride is also called berberine hydrochloride. Berberine can resist pathogenic microorganisms and have inhibitory effects on a variety of bacteria such as Shigella, Mycobacterium tuberculosis, Pneumococcus, Salmonella typhi and Diphtheria bacillus, among which Shigella has the most effect. Strong, commonly used to treat bacterial gastroenteritis, dysentery and other gastrointestinal diseases. Clinically, it is mainly used to treat bacillary dysentery and gastroenteritis, and it has less side effects...

Claims

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Application Information

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IPC IPC(8): C07D455/03
CPCC07D455/03
Inventor 唐成贵
Owner 佑华制药(乐山)有限公司
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