Preparation method of bromhexine hydrochloride

A technology of bromhexine hydrochloride and dibromobenzyl alcohol, which is applied in the novel preparation field, can solve the problems of low product yield, serious environmental pollution, complicated post-treatment, etc., and achieve improved yield and purity, good purity, and reduced The effect of the reaction step

Active Publication Date: 2014-08-27
JIANGXI DONGFU PHARMA CO LTD
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Problems solved by technology

[0008] In the method of the above-mentioned prior art, the reaction route is too long, using highly toxic reagents such as: liquid bromine, phosgene, etc., and the post-treatment is complicated, the product yield is not high, and the environmental pollution is serious

Method used

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  • Preparation method of bromhexine hydrochloride
  • Preparation method of bromhexine hydrochloride

Examples

Experimental program
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Effect test

Embodiment

[0031] (1) 2-amino-3,5-dibromobenzyl alcohol

[0032] Add 2.5g of 2-amino-3,5-dibromobenzaldehyde into 25ml of solvent ethanol, and slowly add sodium borohydride solid (NaBH 4 ) 0.16g, keep the reaction at room temperature for 3 hours, after TLC detects that the reaction raw materials have basically disappeared, add water to dilute, use hydrochloric acid to acidify, adjust the pH to 5-6, continue to stir for 20 minutes, filter, wash with water, and vacuum dry to obtain Near white solid 2-amino-3,5-dibromobenzyl alcohol, melting point 152°C.

[0033] (2) 2-amino-3,5-dibromo-N-cyclohexyl-N-methylbenzylamine hydrochloride (bromhexine hydrochloride)

[0034] Add 2g (about 7.12 mmol) of 2-amino-3,5-dibromobenzyl alcohol into 15ml of tetrahydrofuran (THF), and slowly add solid phosgene (triphosgene) in batches at 0-5°C under stirring conditions 0.72g, use sodium bicarbonate solution to absorb the HCl generated by the system, react at a temperature of 0-5°C for 2 hours, slowly add ...

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Abstract

The invention provides a preparation method of bromhexine hydrochloride. 2-amino-3,5-dibromo benzaldehyde is taken as a raw material, and reduction, amination and salifying are carried out, so that the bromhexine hydrochloride is obtained, wherein amination and salifying are completed in one step, and an intermediate product is not needed to be separated. The preparation method of the bromhexine hydrochloride has the advantages that reaction steps are reduced, and yield and purity of the bromhexine hydrochloride product are improved.

Description

technical field [0001] The invention relates to a novel preparation method of bromhexine hydrochloride. Background technique [0002] Bromhexine Hydrochloride is an antitussive and expectorant agent, which is used for chronic bronchitis, tuberculosis, silicosis and other diseases, as well as symptoms such as difficulty in coughing up phlegm and blood after surgery, and can also promote the discharge of bronchial contrast media. The chemical name of bromhexine hydrochloride is 2-amino-3,5-dibromo-N-cyclohexyl-N-methylbenzylamine hydrochloride, and the molecular formula is C 14 h 21 N 2 Br 2 Cl, its structural formula is as follows: [0003] [0004] At present, the preparation method of bromhexine hydrochloride mainly contains following several kinds: [0005] Method 1: Using 2-nitrobenzyl bromide as a raw material, after amination reaction with N-methylcyclohexylamine, the nitro group is reduced to an amino group with a reagent such as hydrazine hydrate to obtain N-(...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/52C07C209/22
Inventor 余中华
Owner JIANGXI DONGFU PHARMA CO LTD
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