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Preparation method for N-(2-phenyl)ethyl-2-[(2,2-dimethoxyethyl)amino]acetamide halate

A technology of aminoacetamide and dimethoxyethyl, applied in the fields of chemistry and medicinal chemistry, can solve the problems of high production cost, unstable product, large consumption, etc., and achieves reduced production cost, good stability and mild reaction conditions. Effect

Inactive Publication Date: 2009-09-23
SHANGHAI INST OF PHARMA IND CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method yield is low (67%), and the consumption of raw material aminoacetaldehyde dimethyl ether is big, and production cost is high, and the product obtained is unstable, very easy to absorb water

Method used

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  • Preparation method for N-(2-phenyl)ethyl-2-[(2,2-dimethoxyethyl)amino]acetamide halate
  • Preparation method for N-(2-phenyl)ethyl-2-[(2,2-dimethoxyethyl)amino]acetamide halate

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Experimental program
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Effect test

Embodiment 1

[0016] After mixing 35.6 grams of N-(2-phenyl)ethyl-2-aminoacetamide, 16 grams of sodium carbonate, 2.76 grams of tetrabutylammonium chloride, 100 milliliters of methyl isobutyl ketone and 100 milliliters of water, heat To 90°C, add dropwise a mixture of 25 g of chloroacetaldehyde dimethyl ether and 50 ml of methyl isobutyl ketone, keep the temperature at 90°C for 5 hours, cool to room temperature, separate the water layer, and wash the organic layer with water Once, evaporate methyl isobutyl ketone to dryness to obtain a yellow oil, which is dissolved in 100 ml of dichloromethane, and dry hydrogen chloride gas is introduced at 0-5°C to pH = 1-2, filtered, and the filter cake is washed with a small amount of frozen distillate After washing with methyl chloride, it was dried to obtain 42.0 g of white solid (HPLC content greater than 98%), yield: 69.7%.

Embodiment 2

[0018] After mixing 17.8 grams of N-(2-phenyl)ethyl-2-aminoacetamide, 8.0 grams of sodium carbonate, 1.38 grams of tetrabutylammonium chloride, 50 milliliters of methyl isobutyl ketone and 50 milliliters of water, cool To 0°C, add dropwise a mixture of 12.5 g of chloroacetaldehyde dimethyl ether and 30 ml of methyl isobutyl ketone, keep the temperature at 0°C for 2 hours after dropping, then rise to room temperature and stir overnight, separate the water layer, and organic The layer was washed once with water, evaporated to dryness of methyl isobutyl ketone to obtain a yellow oil, which was dissolved in 50 ml of dichloromethane, and dried hydrogen chloride gas was introduced at 0-5°C to pH = 1-2, filtered, and the filter cake was used Wash with a small amount of frozen dichloromethane and dry to obtain 20.8 g of white solid (HPLC content greater than 98%), yield: 69.0%.

Embodiment 3

[0020] After mixing 17.8 grams of N-(2-phenyl)ethyl-2-aminoacetamide, 6.0 grams of sodium hydroxide, 1.6 grams of cetyltrimethylammonium chloride, 50 milliliters of dichloromethane and 50 milliliters of water , add dropwise a mixture of 12.5 g of chloroacetaldehyde dimethyl ether and 30 ml of dichloromethane at room temperature, stir overnight after dropping, separate the water layer, wash the organic layer once with water, and concentrate part of the dichloromethane, then place in 0- Pass dry hydrogen chloride gas at 5°C to pH=1-2, filter, wash the filter cake with a small amount of frozen dichloromethane and dry to obtain 19.7 g of white solid (HPLC content greater than 98%), yield: 65.4%.

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Abstract

The invention discloses a preparation method for N-(2-phenyl)ethyl-2-[(2,2-dimethoxyethyl)amino]acetamide halite, which comprises the following steps: mixing N-(2-phenyl)ethyl-2-amino acetamide and aminoacetaldehyde dimethyl acetal, and in the presence of alkali and a phase transfer catalyst, reacting the mixture in an organic solvent and a water system; and separating an organic layer after finishing the reaction, boiling off a menstruum, and introducing dried chlorine hydride or hydrogen bromide gas after the obtained concentrate is dissolved by a solvent to salify. The method has the following advantages of simple operation, mild reaction conditions, and higher yield (the yield can be up to 72 percent); and the product is non-hygroscopic after being placed in air for a long time, has good stability, and simultaneously is favorable for industrial production because the production cost is greatly reduced compared with the prior art.

Description

technical field [0001] The present invention relates to the field of chemistry, in particular to the field of medicinal chemistry. More specifically, the present invention provides a kind of N-(2-phenyl)ethyl-2-[(2,2-dimethoxyethyl)amino]acetamide Halogen salt preparation method. Background technique [0002] Praziquantel is a broad-spectrum antiparasitic drug. It has a wide anti-helminth spectrum and is very effective against five major schistosomiasis (Mansoni, Egyptian, Japanese, Mekong and schistosomiasis) diseases. In addition, it also has a killing effect on lung fluke, clonorchis sinensis, hydatid, cysticercosis, sparganum monstii, fasciola gingivalis, tapeworm and so on. Its action is characterized by high curative effect, small dose, short course of treatment, fast metabolism, low toxicity and convenient oral administration. The advent of praziquantel is a major breakthrough in the chemotherapy of parasitic diseases, and now it has become the drug of choice for t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C237/08C07C231/12
Inventor 赵建宏马维勇
Owner SHANGHAI INST OF PHARMA IND CO LTD
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