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Method for preparing methoxamine hydrochloride

A technology of methoxamine hydrochloride and a synthesis process, which is applied in the field of preparation of cardiovascular drug methoxamine hydrochloride, can solve the problems of difficult gas flow control, unstable yield, long reaction steps, etc., and achieves fewer reaction steps, simple operation, The effect of mild operating conditions

Active Publication Date: 2013-03-20
WUHAN WUYAO PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] This route has longer reaction steps and more complicated operation. In the oximation reaction, hydrogen chloride gas and methyl nitrite occur simultaneously, the gas flow rate is difficult to control, and the yield is unstable.

Method used

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  • Method for preparing methoxamine hydrochloride
  • Method for preparing methoxamine hydrochloride
  • Method for preparing methoxamine hydrochloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Embodiment 1: the synthesis of compound III

[0023] 1g (0.005mol) p-methoxy bromopropiophenone (compound II) was dissolved in 15ml butyl acetate and placed in a 100ml three-neck flask, 1.1g (0.0069mol) bromine was dissolved in 5ml butyl acetate, and slowly Add dropwise to the reaction solution, TLC monitors the reaction end point, add water and stir for 15 minutes, separate layers, extract with ethyl acetate, wash with water until neutral, dry, and dissolve, the reddish-brown oily substance, crystals precipitate out after adding petroleum ether, filter, and dry to obtain 1.1 g of light yellow crystals (compound III), yield 78.6%

Embodiment 2

[0024] Embodiment 2: the synthesis of compound IV

[0025] Add 0.1g (0.37mmol) 2-bromo-1-(2,5-dimethoxyphenyl) acetone (compound III), 2ml ethanol, 0.16g (0.73mmol) bis-tert-butylcarbonylamine to a 50ml flask, 1ml of 8% NaOH solution was heated to reflux, and the end point of the reaction was monitored by TLC. Add water and stir for 15 minutes, extract with ethyl acetate, wash with water, dry, and dissolve to obtain 0.13 g of yellow solid (Compound IV), yield 86.67%

Embodiment 3

[0026] Embodiment 3: the synthesis of compound V

[0027] Add 0.17g (0.4mmol) 2-bis-tert-butylcarbonylamine-1-(2,5-dimethoxybenzene) acetone (compound IV) to a 50ml flask, add 0.06g (1.7mmol) in batches to 20ml ethanol ) sodium borohydride, stirred at room temperature, TLC monitored the reaction end point, the mixture was poured into water and stirred for 15 minutes, extracted with ethyl acetate, washed with water, dried and precipitated to obtain 0.14 g of light yellow solid (Compound V), yield 82.35%

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Abstract

The invention provides a method for preparing methoxamine hydrochloride. 4'-methoxypropiophenone is taken as a raw material, is subjected to bromination, condensation, hydrogenation and salt forming reaction to obtain the methoxamine hydrochloride; and the 4'-methoxypropiophenone is utilized to prepare 2-bromine-1-(2, 5-dimethoxybenzene) acetone at first, the 2-bromine-1-(2, 5-dimethoxybenzene) acetone is then reacted with 2-di-tert-butyl carbonylamine to obtain 2-di-tert-butyl carbonylamine-1-(2, 5-dimethoxybenzene) acetone, the 2-di-tert-butyl carbonylamine-1-(2, 5-dimethoxybenzene) acetone is subjected to hydrogenation reduction to obtain 2-di-tert-butyl carbonylamine-1-(2, 5-dimethoxybenzene) propyl alcohol, and finally, the 2-di-tert-butyl carbonylamine-1-(2, 5-dimethoxybenzene) propyl alcohol is reacted with hydrochloric acid to obtain the methoxamine hydrochloride. The method has the advantages of short reaction steps, moderate operation conditions, convenience and suitability for industrial production.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a preparation method of cardiovascular medicine methoxamine hydrochloride. [0002] Background technique [0003] Methoxamine hydrochloride is an α-receptor agonist with obvious vasoconstriction. It can increase both systolic and diastolic blood pressure by increasing peripheral resistance, but has no exciting effect on the heart. It is also suitable for preventing hypotension and supraventricular paroxysmal tachycardia before spinal anesthesia caused by massive bleeding, trauma, and surgery. It can also be used for postoperative circulatory failure and hypotensive shock caused by peripheral circulatory failure. [0004] The existing industrial production route of methoxamine mainly takes hydroquinone as raw material, and dimethyl sulfate, propionyl chloride, and oximation reduction obtain the target product, and its synthetic route is as follows: [0005] [...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C217/70C07C213/08
Inventor 皮金红冯珂丁友友魏金维潘文清谢国范
Owner WUHAN WUYAO PHARMA
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