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Chemical synthesis method of N-(4-chlorobenzoyl)-tyramine

A chlorobenzoyl, chemical synthesis technology, applied in the field of chemical synthesis of N--tyramine, can solve the problems of high sealing requirements, high cost, corrosion and other problems of reaction equipment, achieve great implementation value and social and economic benefits, eliminate Large hidden dangers in process safety, simple and safe operation

Active Publication Date: 2009-06-03
ZHEJIANG JIUZHOU PHARM CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] The disadvantages of the above route and reaction are: the material 4-chlorobenzoyl chloride used to synthesize the target product is difficult to obtain: the cost of 4-chlorobenzoyl chloride is relatively high, and if it is prepared by conventional methods, chlorine must be used in the reaction process. sulfoxide, but thionyl chloride (SOCl 2 ) is an acid chloride reagent, which is severely corrosive, pollutes the environment, and has high requirements for equipment; moreover, thionyl chloride is a strictly controlled chemical weapon stipulated by the United Nations. Therefore, transportation and use must be strictly controlled, and the sealing requirements of reaction equipment are high. The investment is also larger

Method used

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  • Chemical synthesis method of N-(4-chlorobenzoyl)-tyramine

Examples

Experimental program
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Effect test

Embodiment 1

[0033] Add 50g of tyramine, 5g of boric acid, 58g of p-chlorobenzoic acid, 460ml of xylene into a clean 1000ml flask equipped with a water separator, stir and heat to reflux with water for 9.5 hours; distill xylene under reduced pressure; add 75ml of ethanol , heating to reflux for beating for 1 hour; cooling and suction filtration; drying to obtain 95.3 g of the target product with a yield of 95.1%.

Embodiment 2

[0035] Add 40g of tyramine, 4g of metaboric acid, 50g of p-chlorobenzoic acid, and 460ml of xylene into a clean 1000ml flask equipped with a water separator, stir and heat under reflux with water for 8 hours; distill xylene under reduced pressure; add ethanol 75ml, heated to reflux for beating for 1 hour; cooled and suction filtered; dried to obtain 74.9g of the target product with a yield of 93.4%.

Embodiment 3

[0037] Add 30g of tyramine, 3g of boric acid, 41g of p-chlorobenzoic acid, 420ml of xylene into a clean 1000ml flask equipped with a water separator, stir and heat under reflux with water for 12 hours; distill xylene under reduced pressure; add 75ml of ethanol , heated to reflux for beating for 1 hour; cooled and suction filtered; dried to obtain 56.9 g of the target product with a yield of 94.7%.

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Abstract

The invention discloses a chemical synthesis method of N-(4-chlorobenzoyl)-tyramine with a structure as shown in formula (I), and the method takes tyramine with a structure as shown in formula (II) and p-chlorobenzoic acid with a structure as shown in formula (II) as raw materials for full reaction to obtain the N-(4-chlorobenzoyl)-tyramine. Compared with the prior art, the raw materials used by the invention are cheap and easy to obtain (eliminating the use of the raw materials prepared by thionyl chloride), the invention basically eliminates the problems of great safety hidden troubles, serious pollution caused by three wastes, and the like of the traditional process and reduces the production cost; meanwhile, the invention has simple and safe operation, reasonable process conditions and high reaction yield, thereby having great implementing value and social and economic benefits.

Description

technical field [0001] The invention relates to a chemical synthesis method of N-(4-chlorobenzoyl)-tyramide. Background technique [0002] N-(4-chlorobenzoyl)-tyramide, molecular formula: C 15 h 14 ClNO 2 , molecular weight: 275.7, CAS number: 41859-57-8, English name: N-(4-Chlobenzoyl)-tyramine, its structure is shown in formula (I): [0003] [0004] It is an important chemical intermediate and has a very wide range of uses in the fields of medicine and chemical synthesis. [0005] The method for synthesizing N-(4-chlorobenzoyl)-tyramine in one step in the prior art generally adopts tyramine (4-hydroxyphenylethylamine) as starting raw material, reacts with 4-chlorobenzoyl chloride, and the reaction equation as follows: [0006] [0007] The published literature on this route is as follows: [0008] 1. British patent GB 2,021,575, publication date: December 5, 1979, name: α-[4-(4-chlorobenzoyl)aminoethylphenoxy]-isobutyric acid (Process for the preparation of a...

Claims

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Application Information

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IPC IPC(8): C07C233/75C07C231/02
Inventor 邬卫国张美君陈晓艳周志敏
Owner ZHEJIANG JIUZHOU PHARM CO LTD
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