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A kind of synthetic method of methoxyphenamine hydrochloride

A technology of methoxamine hydrochloride and a synthesis method, which is applied in the field of synthesis of pharmaceutical raw materials and chemical intermediates, can solve the problems of easy explosion, high risk, increased production cost, etc., and achieves avoiding explosion, mild reaction conditions, and reducing reaction time. cost effect

Active Publication Date: 2018-05-18
CHANGZHOU RUIMING PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] In the above-mentioned method for reacting o-methoxyphenylacetone and methylamine methanol, platinum oxide, platinum dichloride, and palladium carbon will be used as catalysts, which are expensive and will significantly increase production costs; and in the hydrogenation process , prone to explosion, high risk

Method used

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  • A kind of synthetic method of methoxyphenamine hydrochloride

Examples

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Embodiment 1

[0023] Add 80kg of o-methoxyphenylacetone and 240g of methanol into the reactor, stir and mix at 25°C for 30 minutes, pass through methylamine gas, control the temperature at 20°C, and ventilate for about 11 hours, then react to o-methoxy If the concentration of phenylacetone is lower than 5% of the reaction solution, stop the aeration.

[0024] Cool down to -8°C, add 14.4kg of sodium borohydride in portions, stir for 1 hour, add 50kg of water to destroy unreacted sodium borohydride; vacuum distill to remove the solvent, then add 100kg of water, stir for 1.5 hours, and let stand for 1 hour. The water separator was opened to separate the water layer, and the water was distilled off by vacuum distillation.

[0025] Add 64kg of absolute ethanol, stir for 1 hour, filter, cool down to below 0°C, add hydrochloric acid / ethanol solution dropwise to the filtrate to adjust PH=2; at -8°C, crystallize for 12 hours, and filter to obtain crude methoxyphenamine hydrochloride , after recryst...

Embodiment 2

[0027] Add 80kg of o-methoxyphenylacetone and 280kg of methanol into the reactor, stir and mix at 25°C for 30 minutes, pass through methylamine gas, control the temperature at 35°C, and ventilate for about 13 hours, then react to o-methoxy If the concentration of phenylacetone is lower than 5% of the reaction solution, stop the aeration.

[0028] Cool down to -10°C, add 16kg of sodium borohydride in portions, stir for 1 hour, add 50kg of water to destroy unreacted sodium borohydride; remove the solvent by vacuum distillation, then add 100kg of water, stir for 1.5 hours, stand for 1 hour, open The water layer is separated by a water separator, and the water is evaporated by vacuum distillation.

[0029] Add 80 kg of absolute ethanol, stir for 1 hour, filter, cool down to below 0°C, add hydrochloric acid / ethanol solution dropwise to the filtrate to adjust PH=3; at -8°C, crystallize for 12 hours, and filter to obtain crude methoxyphenamine hydrochloride , after recrystallization...

Embodiment 3

[0031] Add 80kg of o-methoxyphenylacetone and 264kg of methanol into the reactor, stir and mix at 25°C for 30 minutes, pass through methylamine gas, control the temperature at 30°C, and ventilate for about 12 hours, then react to o-methoxy If the concentration of phenylacetone is lower than 5% of the reaction solution, stop the aeration.

[0032] Cool down to -9°C, add 15.2kg of sodium borohydride in portions, stir for 1 hour, add 50kg of water to destroy unreacted sodium borohydride; vacuum distillation to remove the solvent, then add 100kg of water, stir for 1.5 hours, and let stand for 1 hour. The water separator was opened to separate the water layer, and the water was distilled off by vacuum distillation.

[0033] Add 72 kg of absolute ethanol, stir for 1 hour, filter, cool down to below 0°C, add hydrochloric acid / ethanol solution dropwise to the filtrate to adjust PH = 2; at -8°C, crystallize for 12 hours, filter to obtain crude methoxyphenamine hydrochloride , after re...

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Abstract

The invention relates to a synthesis method of methoxyphenamine hydrochloride. The method comprises the following steps: synthesizing o-methoxyphenyl oxime from o-methoxyphenyl acetone and monomethyl amine in an organic solvent; reducing the o-methoxyphenyl oxime by using sodium borohydride or potassium borohydride to obtain methoxyphenamine hydrochloride free alkali; and adding a hydrochloric acid / ethanol solution into the methoxyphenamine hydrochloride free alkali to regulate the pH value to 2-3, and carrying out separation and purification to obtain the methoxyphenamine hydrochloride. The sodium borohydride or potassium borohydride is adopted, thereby greatly lowering the reaction cost. The reaction conditions are mild, thereby avoiding the possibility of hydrogenation gas reaction explosion and the palladium / carbon, platinum or any other noble metal catalyst required by the hydrogenation technique, and implementing industrialization.

Description

technical field [0001] The invention relates to the field of synthesis of pharmaceutical raw materials and chemical intermediates, in particular to a synthesis method of methoxyphenamine hydrochloride. Background technique [0002] Methoxyphenamine hydrochloride, chemical name: 2-methoxy-N, the hydrochloride salt of α-dimethylphenethylamine, is a β-adrenergic receptor agonist, which has the effect of relaxing bronchial smooth muscle and relieving bronchospasm. Its anti-asthma effect is stronger than that of ephedrine, but it is weaker in central nervous system and cardiovascular aspects. [0003] The current reported synthesis methods mostly use metal-catalyzed hydrogenation reactions: [0004] Heinzelman R.V. reported a synthetic method (Journal of the American Chemical Society, 1953,75:921-5), o-methoxyphenylacetone, platinum oxide as catalyst, methylamine dissolved in methanol (7.7% concentration), Pressurized hydrogenation under the condition of 3 atmospheric pressure ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C213/00C07C213/02C07C217/60C07C249/02C07C251/16
CPCC07C213/00C07C213/02C07C249/02C07C217/60C07C251/16
Inventor 史卫明王小亮戴文昌
Owner CHANGZHOU RUIMING PHARMA
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