Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Preparation method for bromhexine hydrochloride

A technology of bromhexine hydrochloride and bromhexine, applied in the field of preparation of bromhexine hydrochloride, which can solve the problems of large environmental pollution, harsh reaction, and high cost of intermediates

Active Publication Date: 2019-03-29
GUANGZHOU YIPINHONG PHARMA +5
View PDF9 Cites 4 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0020] In summary, in the above or other preparation routes, there are high cost of raw materials or intermediates, unstable intermediates, harsh reactions, large environmental pollution, cumbersome post-processing, or low purity of the obtained API

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Preparation method for bromhexine hydrochloride
  • Preparation method for bromhexine hydrochloride
  • Preparation method for bromhexine hydrochloride

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0055] The invention provides a kind of preparation method of bromhexine hydrochloride, comprising the following steps:

[0056] (1) carry out bromination reaction after mixing 2-aminobenzoic acid ester compound, bromine, oxidizing agent and mixed solvent, generate 3,5-dibromo-2-aminobenzoic acid ester;

[0057] (2) Mixing the obtained 3,5-dibromo-2-aminobenzoic acid ester, a catalyst, a reducing agent and a solvent to perform a reduction reaction to generate 3,5-dibromo-2-aminobenzyl alcohol;

[0058] (3) carry out condensation reaction after the gained 3,5-dibromo-2-aminobenzyl alcohol, N-methylcyclohexylamine, mixed catalyst and solvent are mixed, generate bromhexine;

[0059] (4) Gained bromhexine and hydrochloric acid are carried out salt-forming reaction in solvent, generate bromhexine hydrochloride.

[0060] The invention mixes 2-aminobenzoic acid ester compounds, bromine, oxidizing agent and mixed solvent to perform bromination reaction to generate 3,5-dibromo-2-amino...

Embodiment 1

[0102] The raw materials in this example are all commercially available.

[0103] Synthesis of methyl 3,5-dibromo-2-aminobenzoate:

[0104] 26.50 kg of dichloromethane, 8.0 kg of purified water, and 3.02 kg of methyl 2-aminobenzoate were successively added into a 100L double-layer glass reactor, and stirred evenly. At room temperature, a solution of bromine (3.83 kg) in dichloromethane (5.3 kg) was slowly added to the reaction solution obtained above. Continue to stir for 10 minutes after the addition is complete, slowly add 2.50 kg of 30% hydrogen peroxide solution to the reaction solution, stir for 6 hours after the reaction is complete, slowly add 3.5 kg of 20% sodium sulfite solution to the reaction solution to quench the reaction, and separate phases , the organic phase was extracted once with 8.0 kg of purified water, the aqueous phase was extracted twice with dichloromethane, the organic phases were combined, the organic phase was concentrated under reduced pressure un...

Embodiment 2

[0136] The 3.02kg 2-aminobenzoic acid methyl ester among the embodiment 1 is replaced by 3.3kg 2-aminobenzoic acid ethyl ester, other conditions are exactly the same, finally bromhexine hydrochloride can be successfully prepared, and the yields of each step are equivalent.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention belongs to the field of organic synthesis and provides a preparation method for bromhexine hydrochloride. According to the invention, 2-aminobenzoic ester compounds are taken as raw materials and take part in bromination reaction, reduction reaction, condensation reaction and salt forming reaction, so as to acquire bromhexine hydrochloride. The preparation method has the advantages of short synthesis route, low cost, stable intermediate, no pollution to environment, high purity, high yield, reaching officinal standard and suitability for industrial expanded production.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to a preparation method of bromhexine hydrochloride. Background technique [0002] Bromhexine hydrochloride, its chemical name is: N-methyl-N-cyclohexyl-2-amino-3,5-dibromobenzylamine hydrochloride, drug aliases: bromhexyl ammonium, benzyl cyclohexyl ammonium bromide , Bishouping, bromhexine hydrochloride, Bixiaophlegm, Bishuping, Bromhexylamine. This product is white or off-white crystalline powder; odorless and tasteless. This product is slightly soluble in ethanol or chloroform, very slightly soluble in water. This product can directly act on bronchial glands, promote the release of lysosomes of mucus secreting cells, and make the sticky sugar fibers in sputum differentiate and crack; it can also inhibit the synthesis of acid glycoproteins in mucous glands and goblet cells, making them Secrete low-viscosity small molecule glycoproteins, thereby reducing the viscosity...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/52C07C209/16C07C209/74C07C229/56C07C227/16C07C215/68C07C213/00
CPCC07C209/16C07C209/74C07C213/00C07C227/16C07C2601/14C07C229/56C07C215/68C07C211/52
Inventor 李捍雄兰小兵晏鑫星
Owner GUANGZHOU YIPINHONG PHARMA
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com