The preparation method of palmatine

A technology of palmetine and organic solvents, which is applied in the field of chemical synthesis of broad-spectrum antibacterial drugs, can solve the problems of complicated operation, time-consuming and labor-consuming, and low content, and achieve the effects of protecting the ecological environment, obtaining cheap and easy raw materials, and saving plant resources

Active Publication Date: 2011-12-21
NORTHEAST PHARMA GRP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Among the patents related to the synthetic method of palmatine, CN1687064A "Synthetic preparation method of antibacterial and anti-inflammatory drug palmatine" patent, CN100526311C "Synthetic method of palmatine" patent, both of these methods have long reaction routes, complicated operations, and low yields. Low cost, high cost, large amount of three wastes, difficult to handle, and great environmental hazards; CN100999522B "Preparation Method of Palmatine" patent, although the synthesis route is short, but has the disadvantages of poor quality and low content, it is not suitable for industrial production
CN102040604A "a synthesis method of palmatine" patent, u...

Method used

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  • The preparation method of palmatine
  • The preparation method of palmatine
  • The preparation method of palmatine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] (1) Weigh 20g of berberine hydrochloride, 300ml of xylene, and 30g of aluminum trichloride into a 1L reaction bottle equipped with a reflux condenser, thermometer, and tail gas absorption device, and keep the reaction temperature at 140°C for about 4 hours. The reaction is over. Cool down, add 300ml of ice water dropwise, stir thoroughly for 1 hour, filter, wash the filter cake with 100ml of water, drain it, and dry it in a vacuum oven at 40°C for 4 hours to obtain 2,3,9,10-tetrahydroxyberberis hydrochloride Base 18.6g, weight yield 93%.

[0021] (2) Get 9g of 2,3,9,10-tetrahydroxy berberine hydrochloride obtained in the above steps and drop into a 250ml reaction bottle, add 40ml of distilled water and stir, add dimethyl sulfate 12ml, add dropwise 10% NaOH solution 60ml, drop At the end of the addition, the PH value was determined to be alkaline, and the temperature was kept at about 30°C for 2 hours, cooled to 5°C and stirred for 2 hours, filtered, washed with a small...

Embodiment 2

[0024] (1) Weigh 20g of berberine hydrochloride, 400ml of xylene, and 60g of boron tribromide are put into a 1L reaction flask equipped with a reflux condenser, a thermometer, and a tail gas absorption device, and keep the reaction temperature at 100°C for the ring-opening reaction, about The 4 hour reaction was complete. Cool down, add 400ml of ice water dropwise, stir thoroughly for 1 hour, filter, wash the filter cake with 100ml of water, drain it, and dry it in a vacuum oven at 40°C for 4 hours to obtain 2,3,9,10-tetrahydroxyberberis hydrochloride Alkali 19g, weight yield 95%.

[0025] (2) Get 9g of 2,3,9,10-tetrahydroxy berberine hydrochloride obtained in the above steps and drop into a 250ml reaction bottle, add 40ml of distilled water and stir, add 20ml of dimethyl sulfate, add dropwise 100ml of 10% NaOH solution, drop At the end of the addition, the PH value was determined to be alkaline, and the temperature was kept at about 40°C for 4 hours, cooled to 5°C and stirre...

Embodiment 3

[0028] (1) Weigh 20 g of berberine hydrochloride, 300 ml of toluene, and 30 g of aluminum trichloride are put into a 1L reaction bottle equipped with a reflux condenser, a thermometer, and a tail gas absorption device, and keep the reaction temperature at 110° C. for ring-opening reaction, about 4 The hour reaction is over. Cool down, add 300ml of ice water dropwise, stir thoroughly for 1 hour, filter, wash the filter cake with 100ml of water, drain it, and dry it in a vacuum oven at 40°C for 4 hours to obtain 2,3,9,10-tetrahydroxyberberis hydrochloride Base 18.8g, weight yield 94%.

[0029] (2) Get 9g of 2,3,9,10-tetrahydroxy berberine hydrochloride obtained in the above steps and drop into a 250ml reaction bottle, add 30ml of distilled water and stir, add 18ml of dimethyl sulfate, add dropwise 90ml of 10% NaOH solution, drop At the end of the addition, the PH value was determined to be alkaline, and the temperature was kept at about 35°C for 4 hours, cooled to 5°C and stirr...

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Abstract

The invention discloses a preparation method of fibrauretin which is applied in the chemical synthesis field of broad-spectrum antibiotics. The preparation method comprises the following steps: adding berberine hydrochloride in an organic solvent, and reacting at 100-150 DEG C under the catalysis of a Lewis acid to remove methylene and obtain an intermediate 2,3,9,10-tetrahydroxyberberine; placing the intermediate 2,3,9,10-tetrahydroxyberberine in a basic solvent to react under the action of a methylating agent at 30-40 DEG C and obtain an intermediate fibrauretin base; and heating the intermediate fibrauretin base in distilled water to dissolve, and adding hydrochloric acid to form the salt and obtain fibrauretin, wherein the organic solvent is selected from one of toluene and xylene, the Lewis acid is selected from one of aluminium chloride, boron tribromide and zinc chloride, and the methylating agent is dimethyl sulfate. The chemical synthesis method is adopted to prepare fibrauretin, thus the plant resource can be saved and the ecological environment can be protected; and berberine hydrochloride is used as the raw material, the raw material is cheap and easily available, the reaction steps of the synthetic route are short and the operations are simple, thus the cost can be saved and the method is suitable for industrial production.

Description

technical field [0001] The invention relates to a preparation method of palmatine in the field of chemical synthesis of broad-spectrum antibacterial drugs. Background technique [0002] Palmatine, also known as palmatine, palmatine, palmitine, and palmatine, is an alkaloid (palmitine) extracted from Rhubarb vine, which belongs to heat-clearing and detoxifying drugs. Palmatine has a broad-spectrum antibacterial and antiviral effect, which can significantly promote the phagocytosis of bacteria by white blood cells, anti-inflammatory and enhance the body's immunity. It is generally used to treat gynecological inflammation, bacillary dysentery, enteritis, respiratory tract and urinary tract infection, surgical infection, conjunctiva diseases such as inflammation. In addition, palmatine also has a protective effect on the myocardium, can enhance myocardial contractility, and has anti-arrhythmic effects. Due to its definite curative effect, palmatine was included in the "Chinese...

Claims

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Application Information

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IPC IPC(8): C07D455/03
CPCY02P20/582
Inventor 张英于河舟刘九知王虹赵会
Owner NORTHEAST PHARMA GRP
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