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Process for synthesizing trigonelline hydrochloride from dimethyl carbonate and nicotinic acid

A technology of trigonelline hydrochloride and dimethyl carbonate, which is applied in the field of synthesis technology of trigonelline hydrochloride, can solve problems such as restricting the application of trigonelline hydrochloride, increasing scientific research and production process risks, etc., and achieves high conversion rate and environmental friendliness. , the effect of simple process steps and conditions

Inactive Publication Date: 2012-01-04
THE SECOND AFFILIATED HOSPITAL ARMY MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, toxic substances such as dimethyl sulfate or halomethane are used, which increases the risk of scientific research and production process, and also restricts the application of trigonelline hydrochloride as a pharmaceutical raw material and additive

Method used

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  • Process for synthesizing trigonelline hydrochloride from dimethyl carbonate and nicotinic acid
  • Process for synthesizing trigonelline hydrochloride from dimethyl carbonate and nicotinic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Add 49.24 g of nicotinic acid (0.40 mol) to a 100 ml three-necked round-bottom flask with a reflux condenser and stirring, use 67.41 ml (0.80 mol) of dimethyl carbonate as the solvent and stir until dissolved, add 55.28 g of K 2 CO 3 (0.40 mol) and continue to stir for 10 minutes, heated in a water bath to control the temperature at 50°C, and monitored the reaction by thin layer chromatography (TLC) during the reaction. After the reaction, the potassium carbonate K was removed by centrifugation. 2 CO 3 , the pressure is 150-260 Pa, the liquid phase temperature is 60-85 ° C, and the unreacted solvent dimethyl carbonate is removed by concentration under reduced pressure. The residual solid was dissolved with 4 mol / L hydrochloric acid and the pH was adjusted, and the solvent was removed under reduced pressure. Add an appropriate amount of anhydrous methanol to the residual solid and shake thoroughly, and then centrifuge to remove insoluble matter after standing still. ...

Embodiment 2

[0018] Add 49.24 g of nicotinic acid (0.40 mol) to a 100 ml three-necked round-bottom flask with a reflux condenser and stirring, use 33.6 ml (0.88 mol) of dimethyl carbonate as the solvent and stir until dissolved, add 55.28 g of K 2 CO 3 (0.40 mol) and continue to stir for 10 minutes, heated in a water bath to control the temperature at 50°C, and monitored the reaction by thin-layer chromatography during the reaction. After the reaction, the potassium carbonate K was removed by centrifugation. 2 CO 3 , the pressure is 150-260 Pa, the liquid phase temperature is 60-85 ° C, and the unreacted solvent dimethyl carbonate is removed by concentration under reduced pressure. The residual solid was dissolved with 4 mol / L hydrochloric acid and the pH was adjusted, and the solvent was removed under reduced pressure. Add an appropriate amount of anhydrous methanol to the residual solid and shake thoroughly, and then centrifuge to remove insoluble matter after standing still. The fi...

Embodiment 3

[0020] Add 49.24 g of nicotinic acid (0.40 mol) to a 100 ml three-necked round-bottomed flask with a reflux condenser and stirring, stir in 33.6 ml (0.88 mol) dimethyl carbonate until dissolved, add 66.34 g of K 2 CO 3 (0.48 mol) and continue to stir for 10 minutes, heated in a water bath to control the temperature at 50°C, and monitored the reaction by thin-layer chromatography during the reaction. After the reaction, the potassium carbonate K was removed by centrifugation. 2 CO 3 , the pressure is 150-260 Pa, the liquid phase temperature is 60-85 ° C, and the unreacted solvent dimethyl carbonate is removed by concentration under reduced pressure. The residual solid was dissolved with 4 mol / L hydrochloric acid and the pH was adjusted, and the solvent was removed under reduced pressure. Add an appropriate amount of anhydrous methanol to the residual solid and shake thoroughly, and then centrifuge to remove insoluble matter after standing still. The filtrate was concentrat...

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Abstract

The invention relates to a process for synthesizing trigonelline hydrochloride from dimethyl carbonate and nicotinic acid. The process comprises the following steps of: reacting the nicotinic acid and the dimethyl carbonate in the presence of a catalyst K2CO3, after completely reacting, filtering and removing the K2CO3 and other undissolved substances, and decompressing, concentrating and removing the solvent, namely the dimethyl carbonate; dissolving the remained solid by using 4 mol / L of hydrochloric acid, adjusting pH to 2-3, and decompressing and removing the solvent; dissolving the remained solid by using proper absolute methanol, and filtering and removing the undissolved substances after standing; concentrating and crystallizing the filtrate, filtering to obtain solid, re-crystallizing the solid by using ethanol with a certain concentration, and obtaining the product. According to the process disclosed by the invention, the green methylated reagent, namely the dimethyl carbonate, for substituting the methylated reagents, such as dimethyl sulphate, halomethane and the like, which are poisonous on human bodies and risky on the environment, is reacted with the nicotinic acid; the green trigonelline hydrochloride is synthesized; the process condition is simple; the conversion rate of the nicotinic acid is high; the average substitution degree of the product is high; and the method is environment-friendly.

Description

technical field [0001] The present invention relates to a synthesis process of trigonelline hydrochloride, in particular to a process for synthesizing green trigonelline hydrochloride by using green methylating reagent dimethyl carbonate instead of methylating reagents such as dimethyl sulfate or halomethane which are toxic to human body and risky to the environment. A process for synthesizing trigonelline hydrochloride from dimethyl carbonate and nicotinic acid. Background technique [0002] Trigonelline exists in the seeds of legumes, the fruits of cucurbits and pumpkins, and various plants such as coffee beans and potatoes. It has a wide range of pharmacological effects such as lowering blood sugar, lowering blood fat, anti-cancer, promoting nerve tissue regeneration, calming, and anti-oxidation. It can be widely used in drugs, additives, etc. The toxic and side effects of trigonelline are extremely low, and it has high safety. Commonly used as trigonelline hydrochlorid...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/803C07D213/80
Inventor 周吉银周世文张定林汤建林徐颖
Owner THE SECOND AFFILIATED HOSPITAL ARMY MEDICAL UNIV
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