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Method for preparing vanillyl acidamide compounds by interfacial reaction

A technology of vanilla amide and interfacial reaction, which is applied in the field of organic compound preparation, can solve the problems of poor solubility and difficulty in obtaining yield, and achieve the effect of high product purity and simple synthesis process

Active Publication Date: 2009-08-12
上海联陆实业股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, due to the poor solubility of vanillin in anhydrous systems and the easy hydrolysis of acid chlorides in the presence of water, no matter the reaction system reported so far, whether it is Nelson's anhydrous ether solvent system (also using twice the equivalent price Relatively expensive vanillin), or the Janusz aqueous system (due to the simultaneous use of DMF / THF as a co-solvent, resulting in the formation of an aqueous homogeneous system) is difficult to obtain satisfactory yields

Method used

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  • Method for preparing vanillyl acidamide compounds by interfacial reaction

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Example 1 Preparation of one of the vanillic amide compounds: N-(4-hydroxy-3-methoxybenzyl) octadecylamide

[0016] The acid chloride is octadecanoyl chloride, and the addition amount is 8.5 g.

[0017] Dissolve 5.3g of vanillin hydrochloride in 58g of water, add 7.7g of sodium bicarbonate, stir for 30 minutes at 20°C, add 240g of chloroform, stir for 15 minutes, add a solution formed by 8.5g of octadecanoyl chloride and 60g of chloroform , stirred for 30 minutes, then heated up to 40°C, separated the chloroform layer, extracted the water layer once with 60g chloroform, separated the extracted chloroform layer, merged into the chloroform layer, washed with 5% hydrochloric acid solution, and washed with saturated saline , dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure to obtain 11.3 g of the product N-(4-hydroxy-3-methoxybenzyl) octadecylamide. Yield 96%.

Embodiment 2

[0018] Example 2 Preparation of vanillic amide compound 2: N-(4-hydroxy-3-methoxybenzyl) oleamide

[0019] Except that the acid chloride is oleoyl chloride, the addition is 8.4g, the product is N-(4-hydroxyl-3-methoxybenzyl) oleamide, and the product weight is 11.2g, the remainder is identical to Example 1.

Embodiment 3

[0020] Example 3 Preparation of the third vanillic amide compound: N-(4-hydroxy-3-methoxybenzyl)hexadecanamide

[0021] Except that the acyl chloride is hexadecanoyl chloride, the addition is 8.0g, the product is N-(4-hydroxyl-3-methoxybenzyl)hexadecanamide, the product weight is 10.4g, and the yield is 95%, the other Part is identical to Example 1.

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Abstract

The invention relates to a method for preparing haraella amide-type compound by interface reaction, belonging to the technical field of organic compound preparation. Haraella amine hydrochloride and alkyl or aryl acyl chloride are taken as raw materials, water- chloroform solvent forms a two-phase system, and sodium bicarbonate is used as alkali; the raw materials, the water- chloroform solvent and the sodium bicarbonate react at the room temperature at interface; after the reaction, a chloroform layer is separated out, and the solvent is removed, so that the haraella amide-type compound can be obtained; reaction formula referring to the operation of the method is shown above. The method has the advantages of simple synthesis technique, high product purity, high yield and the like, and is applicable to preparing the haraella amide-type compound which has the functions such as antibacterium, antitumor, analgesis and antiphlogosis, promoting gastric secretion and blood circulation, improving disease-resistant ability of organism and the like; the haraella amide-type compound has wide application prospect in the fields of medicine and pesticide.

Description

technical field [0001] The invention relates to a method for preparing vanilla amide compounds through interfacial reaction, and belongs to the technical field of organic compound preparation. Background technique [0002] Vanilla amide compounds exist in peppers. The saturated and unsaturated compounds with acyl chain length of C10 are called capsaicin and dihydrocapsaicin respectively. They are the main irritating components of peppers and can enhance the secretion of animal catecholamines and energy consumption. , to reduce fat accumulation in animals. In addition to capsaicin, a series of capsaicin derivatives with acyl side chains of different lengths have also been isolated from red peppers. Studies have shown that the C14-C20 capsaicin derivatives are non-irritating, have a good taste, and can still stimulate the release of adrenaline, and the C18-chain capsaicin derivatives can enhance fat metabolism. But these amides with long side chains are very low in capsicum,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C231/02C07C233/18C07C233/73A61P31/00A61P35/00A61P29/00A61P1/04A61P9/00
Inventor 汤杰杨帆单益凡王博孙国平仇文卫
Owner 上海联陆实业股份有限公司
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