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Preparation method of palmatine hydrochloride

A technique for palmatine hydrochloride and berberine hydrochloride, which is applied in the field of synthesis of palmatine hydrochloride, can solve the problems of poor feasibility, unsuitability for large-scale production, and pending development of palmatine hydrochloride, and achieve easy operation and large scale Production and economical applicability, beneficial effect on the protection of natural resources and ecological environment

Active Publication Date: 2018-09-28
YUNNAN BAIYAO GROUP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The method reported in the patent of Shanghai Yizhi Pharmaceutical Technology (the new preparation method of palmatine CN102875545A) has poor feasibility and is not suitable for scale-up production
Therefore, the industrialized preparation method of palmatine hydrochloride still remains to be developed

Method used

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  • Preparation method of palmatine hydrochloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] (1) Weigh 200g of berberine hydrochloride, 1L of toluene and 500g of methanesulfonic acid into a 3L round-bottomed flask equipped with a reflux condenser, thermometer and stirring device. Keep the temperature of the reaction solution at 90°C and stir for about 12 hours. TLC monitors the disappearance of the raw materials, and the stirring is stopped. Add ethanol and stir at reflux for 2 hours. After cooling to room temperature and standing for crystallization, 151 g of 2,3-dihydroxyberberine methanesulfonate was obtained with a yield of 78%.

[0019] (2) Take 100g of the 2,3-dihydroxyberberine methanesulfonate obtained in the above steps and put it into a 3L round bottom flask, add 114g of methyl p-toluenesulfonate and 46g of potassium carbonate, and acetonitrile as the solvent and reflux for 5 hours. TLC monitors the disappearance of the raw materials, and the stirring is stopped. Reduce to room temperature, filter, and wash the filter cake with a small amount of water....

Embodiment 2

[0022] (1) Weigh 200g of berberine hydrochloride, 1L of toluene and 500g of methanesulfonic acid into a 3L round-bottomed flask equipped with reflux condenser, thermometer and stirring device. Keep the temperature of the reaction solution at 90℃. After about 12 hours, TLC Monitor the disappearance of the raw materials and stop stirring. Add ethanol and stir at reflux for 2 hours. After cooling to room temperature and standing for crystallization, 154 g of 2,3-dihydroxyberberine methanesulfonate was obtained with a yield of 80%.

[0023] (2) Take 100g of 2,3-dihydroxyberberine methanesulfonate obtained in the above steps and put it into a 3L round bottom flask, add 600ml of N,N-dimethylformamide to dissolve, add 100ml of dimethyl carbonate and cesium carbonate 109g, after addition, stirred at 140°C for 8 hours, TLC monitored the disappearance of the raw materials, and stopped stirring. It was cooled to room temperature, the solvent was removed, and the precipitated solid was col...

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PUM

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Abstract

The invention discloses a preparation method of palmatine hydrochloride. By adopting a method for synthesizing palmatine hydrochloride from berberine hydrochloride, damage to plant resources caused byextraction of the palmatine hydrochloride from plants and the environmental pollution caused by the use of a large amount of sulfuric acid in an extraction process can be avoided, and the ecologicalenvironment is protected. The preparation method has the advantages of adoption of cheap and readily-available reaction raw materials, avoidance of the use of highly-toxic conventional methylation reagent dimethyl sulfate or iodomethane or bromomethane, short synthetic route, easiness in operation and suitability for industrial production.

Description

Technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a method for synthesizing palmatine hydrochloride using berberine hydrochloride as a raw material. Background technique [0002] Palmatine hydrochloride, also known as yellow rattan, is a quaternary ammonium alkaloid isolated from the roots and stems of Fibrurea recisa Pierre, a plant of the fangchi family. It is widely used in various types of infections and gynecological diseases in clinical practice. At the same time, it has multiple pharmacological effects of broad-spectrum antibacterial, antagonistic, antiviral and strengthening the body's defense function, safe and reliable, and no obvious adverse reactions. Because of its definite curative effect, palmatine hydrochloride was included in the Chinese Pharmacopoeia in 1977, and later included in the Chinese Pharmacopoeia in historical editions. [0003] The broad-spectrum antibacterial and anti-inflammatory pharmacologi...

Claims

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Application Information

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IPC IPC(8): C07D455/03
CPCC07D455/03
Inventor 王明辉李明明邓斌赵智东杨冲生杨志赵守仁
Owner YUNNAN BAIYAO GROUP
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