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Method for preparing nonivamide

A technology for vanillamide and n-nonanoic acid, applied in the field of preparing vanillamide n-nonanoic acid, can solve the problems of low yield, unenvironmental protection, complicated post-processing and the like, achieve simple post-processing, avoid the use of organic solvents, and avoid sodium salts The effect of pollution

Pending Publication Date: 2020-11-03
辽宁雷泰生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The technical problem to be solved by the present invention is to provide a kind of aryl boronic acid as dehydration condensation catalyst, simple process, low cost, high yield, high atom economy, low reaction conditions, high product purity, green and environment-friendly preparation of n-nonanoic acid A new method of vanillic acid to solve the problems of low yield, environmental protection and complex post-treatment in the prior art for preparing n-nonanoic acid vanillic acid

Method used

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  • Method for preparing nonivamide
  • Method for preparing nonivamide

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Experimental program
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Embodiment 1

[0030] The preparation of embodiment 1 aryl boronic acid

[0031] The aryl boronic acid of the present invention is prepared by a prior art method: Synthesis, evaluation and application of novel bifunctional N, N-diisopropylbenzylamine boronic acid catalysts for direct amide formation between carboxylic acids and amines, Green Chemistry, 2008.

Embodiment 2

[0033] Add 2-((N,N-diisopropyl)methyl)phenylboronic acid (0.0327mol, 10mol%) to 200ml methylene chloride in a 500ml three-necked flask, add active Stir with molecular sieves, add 50g (0.327mol) of 3-methoxy-4-hydroxybenzylamine at room temperature, stir and heat to reflux at 40°C, add 43g (0.272mol) of n-nonanoic acid dropwise through the dropping funnel, and keep stirring at reflux for 0.5h After the reaction, cool down to room temperature, add 100ml of water and stir for 5 minutes, then let stand to separate layers, take the oily layer, and distill under reduced pressure at 30°C to recover dichloromethane, stop the reduced-pressure distillation after obtaining a light yellow transparent liquid, cool the remaining liquid to room temperature, and forcefully After stirring for 30 min, 79.6 g of white solid powder was precipitated, with a yield of 95.8% and a purity of 99.3% by HPLC.

[0034] White powder solid analysis

[0035] NMR spectrum characterization: 1H NMR (CDCl3, TM...

Embodiment 3

[0039] Add 2-((N,N-dimethyl)methyl)phenylboronic acid (0.0327mol, 10mol%) to 200ml toluene in a 500ml three-necked flask, add active Stir with molecular sieves, add 50g (0.327mol) of 3-methoxy-4-hydroxybenzylamine at room temperature, stir and heat to reflux at 110°C, add 43g (0.272mol) of n-nonanoic acid dropwise through the dropping funnel, and keep stirring at reflux for 2.5h After the reaction, cool down to room temperature, add 100ml of water and stir for 5 minutes, then let stand to separate layers, take the oily layer, and recover toluene by vacuum distillation at 60°C, stop the vacuum distillation after obtaining a light yellow transparent liquid, cool the remaining liquid to room temperature, and stir vigorously for 30 minutes , 78.9 g of white solid powder was precipitated, the yield was 95.0%, and the HPLC purity was 99.1%.

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Abstract

The invention relates to a method for preparing nonivamide. By using 3-methoxy-4-hydroxy benzylamine and n-nonanoic acid as raw materials and dichloromethane, toluene and fluorobenzene as solvents, adehydration reaction is performed under the catalytic action of arylboronic acid to prepare and synthesize nonivamide. The mole ratio of the 3-methoxy-4-hydroxy benzylamine to the n-nonanoic acid is 1.2:1, the mole amount of the arylboronic acid is 10% of the mole amount of the 3-methoxy-4-hydroxy benzylamine, the dehydration reaction temperature is 25 DEG C to 85 DEG C, and the reaction time is 20 minutes to 5 hours. The method also comprises the following steps: cooling to room temperature after the dehydration condensation reaction is finished, adding water, stirring, standing for layering,taking an oily layer, carrying out reduced pressure distillation until a faint yellow transparent liquid is obtained to recover the organic solvent, cooling the residual liquid to room temperature, and strongly stirring to obtain white solid powder of nonivamide. The method disclosed by the invention is simple in process, low in cost, high in yield, high in atom economy, low in reaction condition, high in product purity, green and environment-friendly.

Description

technical field [0001] The invention relates to a new method for preparing n-nonanoic acid vanillic amide, in particular to a method for preparing n-nonanoic acid vanillic amide by using aryl boronic acid as a catalyst. Background technique [0002] Nonylic acid vanillyamid, also known as synthetic capsaicin, is a natural capsaicin analog, a white or light yellow solid, with a CAS registration number of 404-86-4 and a molecular formula of C 17 h 27 NO 3 , the molecular weight is 293.4, the melting point is 56-58°C, the decomposition temperature is 340°C, and the water solubility is 27ppm at 25°C. Nonanoic acid vanillamide is widely used in the fields of biomedicine, pesticides and functional coatings. In medicine, vanillyl nonanoic acid can be used as a component of drugs for treating rheumatoid arthritis and neuralgia, and because of its antibacterial and anti-inflammatory effects, it can also be used in clinical dermatology. In addition, nonanoic acid vanillylamide can...

Claims

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Application Information

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IPC IPC(8): C07C231/02C07C233/18B01J31/14
CPCC07C231/02B01J31/146
Inventor 朱闻雷
Owner 辽宁雷泰生物科技有限公司
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