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Synthetic method of bromhexine hydrochloride

A technology of bromhexine hydrochloride and a synthesis method, which is applied in the field of chemical synthesis, can solve the problems of strong corrosiveness of workshop equipment, difficult to handle effectively, and is not suitable for large-scale production, and achieves the effects of cost reduction, convenient operation and little pollution

Active Publication Date: 2021-01-08
济南久隆医药科技有限公司 +3
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the literature, thionyl chloride is used as a solvent for chlorination reaction, and the reaction produces a large amount of acid gas, which is difficult to deal with effectively, is highly corrosive to workshop equipment, and is not suitable for large-scale production

Method used

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  • Synthetic method of bromhexine hydrochloride
  • Synthetic method of bromhexine hydrochloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Add 27.9g 2-amino-3,5-dibromobenzaldehyde, 12.5gN-methylcyclohexylamine, 0.84g% 5 palladium carbon and 55g butyl acetate in a 500ml reaction flask and heat up to 100°C, then add dropwise Water formic acid 9.2g, after 1.5h dropwise addition, keep warm at 100-110°C and react for 5h, cool down to 30-35°C, press filter, concentrate the filtrate under reduced pressure until no solvent is evaporated, cool down to 25-30°C, add 25g30 % hydrogen chloride ethanol solution, temperature control 30-35 ℃, stirring reaction 2h-3h, suction filtration, filter cake with 5 times the weight of methanol acetone mixed solution (W methanol: W acetone = 5:1) recrystallization, to obtain the product 37.6kg, yield 91.3%, HPLC purity 99.1%.

Embodiment 2

[0036] Add 27.9g 2-amino-3,5-dibromobenzaldehyde, 12.5gN-methylcyclohexylamine, 0.84g%5 palladium carbon and 55g N,N-dimethylformamide in the 500ml reaction flask and heat up to 100 ℃, add 9.2 g of anhydrous formic acid dropwise, after 1.5 hours of dropping, keep warm at 100-110 ℃ for 5 hours, cool down to 30-35 ℃, press filter, concentrate the filtrate under reduced pressure until no solvent is evaporated, and cool down to 25 -30°C, add 25g of 30% hydrogen chloride ethanol solution, control the temperature at 30-35°C and stir for 2h-3h, filter with suction, and use 5 times the weight of methanol-acetone mixed solution for the filter cake (W methanol:W acetone=5:1) After recrystallization, 37.8kg of the product was obtained, the yield was 91.6%, and the HPLC purity was 99.4%.

Embodiment 3

[0038] Add 27.9kg of 2-amino-3,5-dibromobenzaldehyde, 12.5kg of N-methylcyclohexylamine, 840g of 5% palladium carbon and 55kg of N,N-dimethylformamide into a 100L reaction flask and heat up to 100°C , add 9.2kg of anhydrous formic acid dropwise, after 1.5h of dropwise addition, keep warm at 100-110°C for 5h, cool down to 30-35°C, press filter, concentrate the filtrate under reduced pressure until no solvent is evaporated, cool down to 25-30°C ℃, after adding 25kg of 30% hydrogen chloride ethanol solution, control the temperature at 30-35℃ and stir the reaction for 2h-3h, filter with suction, and recrystallize the filter cake with 5 times the weight of methanol acetone mixed solution (W methanol: W acetone = 5:1) , to obtain product 38.1kg, yield 92.3%, HPLC purity 99.3%.

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Abstract

The invention belongs to the technical field of chemical synthesis, and particularly relates to a synthetic method of bromhexine hydrochloride. The method comprises the following steps: heating 2-amino-3, 5-dibromobenzaldehyde and N-methylcyclohexylamine in a reaction solvent to 100 DEG C, dropwise adding anhydrous formic acid, keeping the temperature at 100-110 DEG C to react for 5 hours after dropwise adding, cooling, concentrating under reduced pressure until no solvent is evaporated, cooling, adding a 30% hydrogen chloride ethanol solution, stirring to react for 2 hours, and carrying out suction filtration; recrystallizing a filter cake to obtain bromhexine hydrochloride. The method has the advantages of concise reaction steps, convenient operation, strong universality to production equipment, no generation of a large amount of acid gas, increase of the product yield to 91%, and substantial reduction of the product cost.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a synthesis method of bromhexine hydrochloride. Background technique [0002] Bromhexine hydrochloride chemical name: N-(2-amino-3,5-dibromobenzyl)-N-methylcyclohexylamine hydrochloride; [0003] Molecular formula: C 14 h 20 Br 2 N 2 HCL; [0004] Molecular weight: 412.6; [0005] Structural formula: [0006] [0007] Bromhexine hydrochloride is a new type of mucolytic expectorant, which can differentiate and crack the mucopolysaccharide fibers in the sputum, reduce the viscosity of the sputum and increase the secretion, so that the sputum becomes thinner, easy to cough up, and clears the respiratory tract. Unobstructed, relieve symptoms. [0008] The patent (CN104003887A) discloses a synthesis process of the compound bromhexine hydrochloride, which specifically involves the reaction of 2-amino-3,5-dibromobenzaldehyde with a reducing agent, and t...

Claims

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Application Information

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IPC IPC(8): C07C211/52C07C209/28C07C209/00C07C209/84
CPCC07C209/28C07C209/00C07C209/84C07C2601/14C07C211/52Y02P20/55
Inventor 马居良郑真真李志远
Owner 济南久隆医药科技有限公司
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