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Synthesis method of betahistine hydrochloride

A technology of betahistine and a synthesis method, applied in the field of synthesis of betahistine hydrochloride, can solve the problems of difficult preparation, medium yield, unsuitable for industrialized production and the like, and achieves easy industrialized production, short reaction route and product yield. High efficiency and purity

Active Publication Date: 2021-11-16
TAIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This reaction uses azide, which is difficult to prepare and explosive, as a raw material, and the yield is moderate, so it is not suitable for industrial production

Method used

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  • Synthesis method of betahistine hydrochloride
  • Synthesis method of betahistine hydrochloride
  • Synthesis method of betahistine hydrochloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] At room temperature, sequentially add 0.06g 5% Pd / C, 15.90g (0.15mol) sodium carbonate, 8.10g (0.12mol) methylamine hydrochloride into a 500mL three-necked flask, depressurize the air and fill it with nitrogen, repeat Three times, the air was replaced with nitrogen. Under nitrogen protection, 12.32 g (0.1 mol) of 2-hydroxyethylpyridine and 280 mL of toluene were injected sequentially. After the addition is complete, heat to 110°C and react for 15h. The reaction solution was cooled to room temperature, 100 mL of water was added, the transition metal catalyst was recovered by suction filtration, and the catalyst was washed with a small amount of ethyl acetate. The filtrate was separated into the organic phase, and the aqueous phase was extracted with ethyl acetate (3 x 30 mL). The organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate, and the organic solvent was recovered by distillation under reduced pressure. The residue was d...

Embodiment 2

[0032] At room temperature, sequentially add 0.12g of 5% Pd / C, 15.90g (0.15mol) of sodium carbonate into a 500mL three-neck flask, depressurize the air and fill it with nitrogen, repeat three times, and replace the air with nitrogen. Under nitrogen protection, 13.7mL (0.16mol) of 40% methylamine aqueous solution, 12.32g (0.1mol) of 2-hydroxyethylpyridine and 210mL of toluene were injected sequentially. After the addition is complete, heat to 90°C and react for 18h. The reaction solution was cooled to room temperature, 100 mL of water was added, the transition metal catalyst was recovered by suction filtration, and the catalyst was washed with a small amount of ethyl acetate. The filtrate was separated into the organic phase, and the aqueous phase was extracted with ethyl acetate (3 x 30 mL). The organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate, and the organic solvent was recovered by distillation under reduced pressure. The resi...

Embodiment 3

[0034] At room temperature, successively add 0.25g nano-nickel powder, 13.60g (0.20mol) sodium formate, 8.10g (0.12mol) methylamine hydrochloride into a 500mL three-necked flask, decompress and extract the air and fill it with nitrogen, repeat three times, use Nitrogen replaced the air. Under nitrogen protection, 12.32 g (0.1 mol) of 2-hydroxyethylpyridine and 280 mL of benzene were injected sequentially. Addition is complete, heated to 80 ° C, the reaction 16h. The reaction solution was cooled to room temperature, 100 mL of water was added, the transition metal catalyst was recovered by suction filtration, and the catalyst was washed with a small amount of ethyl acetate. The filtrate was separated into the organic phase, and the aqueous phase was extracted with ethyl acetate (3 x 30 mL). The organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate, and the organic solvent was recovered by distillation under reduced pressure. The residu...

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Abstract

The invention discloses a synthesis method of betahistine hydrochloride. The synthesis method comprises the following steps: adding a transition metal catalyst and an alkaline reagent into a round-bottom flask at room temperature, and adding methylamine, 2-hydroxyethyl pyridine and an organic solvent under the protection of nitrogen; after feeding is finished, conducting reacting at 40-150 DEG C until a reaction is finished; cooling reaction liquid to room temperature, adding water, performing suction filtration to recover the transition metal catalyst, separating out an organic phase from a filtrate, and extracting a water phase with ethyl acetate three times; merging organic phases, performing washing with saturated salt, conducting drying with anhydrous sodium sulfate, and recovering the organic solvent by reduced-pressure distillation; and dissolving residues with ethanol, introducing dry hydrogen chloride, performing suction filtration, cleaning a filter cake with a proper amount of ethanol, and performing vacuum drying to obtain a product. According to the invention, the transition metal catalyst used in the invention is a commercially available reagent, has high activity, does not need to be prepared additionally, and can be repeatedly used; and the method also has the advantages of usage of cheap and easily available reaction raw materials, shorter reaction route, simplicity and convenience in operation, environmental friendliness, better safety, higher product yield and purity, easiness in industrial production and the like.

Description

technical field [0001] The invention relates to a synthesis method of betahistine hydrochloride, which belongs to the technical field of medicine and chemical industry. Background technique [0002] Betahistine hydrochloride, chemical name N-methyl-2-pyridylethylamine dihydrochloride, as a histamine H 1 Receptor weak agonist, H 3 Strong receptor antagonist for H 2 The receptor has almost no effect, and it is a second-generation antihistamine drug with high efficiency and low toxic and side effects. Betahistine hydrochloride is a drug developed by the Formenti pharmaceutical group in Italy. It was registered and listed in Europe in 1970. It is clinically used as a vasodilator and is mainly used for Meniere's syndrome, vascular Headache and cerebral arteriosclerosis, and can be used to treat acute ischemic cerebrovascular diseases, such as cerebral thrombosis, cerebral embolism, cerebral insufficiency, cerebral arteriosclerosis, etc., for orthostatic vertigo and tinnitus ca...

Claims

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Application Information

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IPC IPC(8): C07D213/38
CPCC07D213/38Y02P20/584
Inventor 洪志章云晓罗梅杨钰莹霍婉华冯贡麒韩娴秦东辉
Owner TAIZHOU UNIV
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