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Synthesis of Important intermediate for mosapride citrate

A technology for mosapride citrate and its intermediates, applied in the field of medicine, can solve the problems affecting the popularization and application of mosapride citrate, difficult to meet the requirements of detection, and high price of iodoethane, so as to improve the synthesis Yield and finished product quality, stable response, and effect on alleviating price issues

Inactive Publication Date: 2004-09-08
LUNAN BETTER PHARMA
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] There are many deficiencies in the existing mosapride citrate raw material synthesis process, mainly in the process of preparing intermediate (1), ethyl iodide reagent is expensive, and the yield is not high, resulting in intermediate (1) ) is close to half of the total cost of mosapride citrate raw material synthesis; the synthesis yield of intermediate (2) is also low, only 40%, and the finished product has poor color, which is dark brown
After reverse purification of the intermediate, it was found that it was the poor quality of the intermediate (2) that caused the final product to often fail to meet the requirements when detecting related substances
Many factors have affected the popularization and application of mosapride citrate

Method used

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  • Synthesis of Important intermediate for mosapride citrate
  • Synthesis of Important intermediate for mosapride citrate
  • Synthesis of Important intermediate for mosapride citrate

Examples

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Effect test

example 1

[0016] Preparation of the intermediate o-hydroxyp-aminobenzoic acid: 100 g of sodium o-hydroxyp-aminobenzoate dihydrate was dissolved in water, stirred, and concentrated hydrochloric acid was added dropwise to 150 g, cooled and filtered to obtain the intermediate o-hydroxyp-aminobenzoic acid, The yield was 96.5%.

[0017]

example 2

[0019] Preparation of intermediate o-hydroxy p-aminobenzoic acid methyl ester: intermediate o-hydroxy p-aminobenzoic acid was dissolved in methanol, stirred, concentrated sulfuric acid was added dropwise, refluxed, methanol was removed, and saturated K 2 CO 3 solution. Cool, stand still, and filter to obtain an off-white solid, which is methyl o-hydroxy p-aminobenzoate, with a yield of 79.7%.

[0020]

example 3

[0022] Preparation of the intermediate o-hydroxy p-acetamidobenzoic acid methyl ester: the intermediate o-hydroxy p-aminobenzoic acid methyl ester is dissolved in glacial acetic acid, stirred, acetic anhydride is added dropwise, and then the solvent is removed, NaOH solution is added to the raffinate, and the The white solid was filtered to obtain the intermediate methyl o-hydroxy p-aminobenzoate with a yield of 80.0%.

[0023]

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Abstract

The present invention relates to the preparation process of important intermediates for Mosapride citrate, 2-oxethyl-4-actamino-5-chlorobenzoic acid and 4-(4-fluorobenzyl-2- aminomethyl morpholine. The intermediate 2-oxethyl-4-actamino-5-chlorobenzoic acid is prepared with amino salicylic acid as initial material and through acidification with hydrochloric acid, esterification with methol, acetylation with acetic anhydride, ethylation, NCS chlorination and alkali hydrolysis. The intermediate 4-(4-fluorobenzyl-2- aminomethyl morpholine is prepared with p-fluorobenzaldehyde and phthalimide as initial material and through dropping at 70-90 deg.c, maintaining at 125-145 deg.c, and post-treatment in ice bath in 2-10 deg.c while adding acetic anhydride through stirring for 10-20hr. The present invention can raise the yield of Mosapride citrate and lower its production cost.

Description

technical field [0001] The invention provides the important intermediate 2-ethoxy-4-acetylamino-5-chlorobenzoic acid (1) of mosapride citrate and the important intermediate 4-(4-fluorobenzyl)-2-ammonia The preparation technology of methylmorpholine (2) belongs to the technical field of medicine. Background technique [0002] With the acceleration of the pace of social life, the improvement of people's living standards and the change of diet structure and other factors, the number of patients with low gastric motility is increasing, and people's quality of life is greatly affected. Mosapride citrate, as the first gastric motility drug without dopamine receptor antagonism, has been widely used at home and abroad because of its good clinical efficacy, low side effects, safety, and high efficiency. , Restoring health provides new options and assistance. [0003] There are many deficiencies in the existing mosapride citrate raw material synthesis process, mainly in the process ...

Claims

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Application Information

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IPC IPC(8): C07C231/10C07C233/54C07D241/04C07D265/30
Inventor 赵志全
Owner LUNAN BETTER PHARMA
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