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Preparation methods of propafenone hydrochloride and intermediate 2'-hydroxydihydrochalcone thereof

A technology of hydroxydihydrochalcone and propafenone hydrochloride, which is applied in the field of preparation of propafenone hydrochloride and its intermediate 2'-hydroxydihydrochalcone, can solve the problem of high operation requirements of production equipment and difficulty in large-scale production Problems such as industrialized production and high price, etc., achieve the effect of low reaction equipment and operation requirements, simple and feasible post-processing

Active Publication Date: 2020-06-02
LINYI UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In the above-mentioned industrialization method, the palladium-carbon used is a precious metal catalyst, which is expensive, and hydrogen is easy to explode in industrial production as a reducing agent, and it is difficult to transport and store. At the same time, the operation requirements for production equipment and workers are relatively high, and it is not easy for large-scale industrial production.

Method used

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  • Preparation methods of propafenone hydrochloride and intermediate 2'-hydroxydihydrochalcone thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0043] Add 300 g of 2'-hydroxychalcone, 300 g of 2-phenyl-benzothiazoline, 900 g of neutral alumina, and 6 L of solvent benzene into the reactor, and react at 80° C. for 10 hours. The reaction was lowered to 25°C, the neutral alumina was removed by suction filtration, and the filter cake was rinsed with a small amount of solvent benzene 300mL. The filtrate was transferred to a reaction kettle, 75 g of potassium hydroxide was added, stirred at room temperature for 4 hours, and 324 g of 2'-hydroxydihydrochalcone potassium salt was obtained after filtration and drying with a yield of 91.6%.

Embodiment 2

[0045] Add 300 g of 2'-hydroxychalcone, 420 g of 2-phenyl-benzothiazoline, 1200 g of acidic alumina, and 9 L of solvent toluene into the reactor, and react at 110° C. for 2 hours. The reaction was lowered to 25°C, the acidic alumina was removed by suction filtration, and the filter cake was rinsed with a small amount of solvent toluene 300mL. The filtrate was transferred to a reaction kettle and 60 g of sodium hydroxide was added, stirred at room temperature for 6 hours, filtered and dried to obtain 325 g of 2'-hydroxydihydrochalcone sodium salt with a yield of 98.0%.

Embodiment 3

[0047] Add 300 g of 2'-hydroxychalcone, 420 g of 2-phenyl-benzothiazoline, 1200 g of acidic alumina, and 9 L of solvent toluene into the reactor, and react at 110° C. for 2 hours. Reduce the reaction to 25°C, remove the acidic alumina by suction filtration, rinse the filter cake with a small amount of solvent toluene 300mL, transfer the filtrate to a reaction kettle, add 60g of sodium hydroxide, stir at room temperature for 6 hours, and obtain 2'-hydroxyl after filtration and drying Dihydrochalcone sodium salt 325g, yield 98.0%. The filter cake obtained in the previous step was acidic alumina and rinsed with a small amount of solvent methanol 300mL. After drying, it was repeatedly applied to the reaction described in Example 3. After 5 times of application, the resulting 2'-hydroxydihydrochalcone sodium salt 315g yield was 94.8 %.

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Abstract

The invention discloses preparation methods of propafenone hydrochloride and an intermediate 2'-hydroxydihydrochalcone thereof. 2-phenyl-benzothiazoline is adopted as a reducing agent to construct a reduction system, carbon-carbon double bonds are reduced, double bonds in a substrate can be efficiently and selectively reduced, and the problem that the propafenone hydrochloride key intermediate 2'-hydroxydihydrochalcone is synthesized by using hydrogen is avoided. The used reducing agent is simple and easily available, and the preparation methods have the advantages of low requirements on reaction equipment and operation, suitableness for industrial production, no hydrogen and noble metals, safety and environmental friendliness.

Description

technical field [0001] The invention relates to a preparation method of propafenone hydrochloride and its intermediate 2'-hydroxydihydrochalcone. Background technique [0002] Propafenone hydrochloride (arrhythmia) as a new class of antiarrhythmic drugs, can act on the atrium, ventricular excitation formation center and excitation conduction system, and can be used to treat ventricular, supraventricular ectopic beats, ventricular and ventricular Superior tachycardia, pre-excitation syndrome, etc., can also be used for ischemic membrane stabilization with competitive beta-receptor blockade. Can reduce myocardial excitability, prolong action potential duration and effective refractory period to prolong conduction. It has the characteristics of fast onset and long-lasting effect. [0003] 2'-Hydroxychalcone is a key intermediate for the preparation of propafenone hydrochloride, and the current industrial production method is mainly prepared by reducing 2'-hydroxychalcone with...

Claims

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Application Information

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IPC IPC(8): C07C49/83C07C45/62C07C45/00C07C217/36C07C213/04C07C213/10
CPCC07C45/62C07C45/00C07D303/23C07D301/00C07C213/04C07C213/10C07C49/83C07C217/36
Inventor 周金川张海娟张淳史晓委赵志龙李海刚
Owner LINYI UNIVERSITY
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