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Preparation method for propranolol

A preparation step, a technology of naphthol, applied in the preparation field of propranolol, can solve the problems of increasing cost and process steps, increasing process steps and costs, and the process is not easy to control, and achieves increasing process steps and costs, and reaction conditions. Not harsh, easy-to-control effects

Active Publication Date: 2018-01-09
KAMP PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Existing synthetic route has following shortcoming: (1) existing synthetic method generally all is to prepare 3-(1-naphthyloxy)-1,2-epoxypropane with naphthol and epichlorohydrin reaction earlier, Then react with isopropylamine to generate the target compound, which increases the process steps and cost; (2) the ring-opening reaction of 3-(1-naphthyloxy)-1,2-propylene oxide with isopropylamine, the yield is not high, Generally only about 50%, the post-treatment needs to recover isopropylamine, which increases the cost and process steps. If you want to increase the yield, it needs to be carried out under the condition of higher than normal pressure, but the process is not easy to control, the post-processing is cumbersome, and there are potential safety hazards , there are certain disadvantages in industrial production

Method used

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  • Preparation method for propranolol
  • Preparation method for propranolol
  • Preparation method for propranolol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Preparation of TM

[0036]

[0037] Naphthol (I) (144.2g, 1mol), epichlorohydrin (113.3, 1.1mol), isopropylamine (90.5g, 1.5mol), tetrabutylammonium bromide (16.6g, 0.05mol) were added to the reaction In the bottle, lower the temperature to about 0°C, then slowly add 10% sodium hydroxide aqueous solution (400g) dropwise to the above reaction flask, after the addition, react at 0°C for 3 hours, then raise the temperature to 100°C and stir the reaction, TLC monitoring After 2 hours of reaction, the temperature was lowered to 0°C, 10% sodium hydroxide aqueous solution (400g) was added dropwise, stirred for 1 hour, filtered, the filter cake was washed with water and drained, dried under reduced pressure, and recrystallized from n-hexane to obtain propranolol (TM ) 233.4 g, yield 90.0%, purity 99.5%.

Embodiment 2

[0039] Naphthol (I) (144.2g, 1mol), epichlorohydrin (113.3, 1.1mol), isopropylamine (90.5g, 1.5mol), tetrabutylammonium bromide (16.6g, 0.05mol) were added to the reaction In the bottle, lower the temperature to about 0°C, then dissolve sodium methoxide (40g) in methanol (360g) and slowly add it dropwise to the above reaction bottle. , TLC monitoring, after 2 hours of reaction, the temperature was lowered to 0°C, 10% sodium hydroxide aqueous solution (400g) was added dropwise, stirred for 1 hour, filtered, the filter cake was washed with water and drained, dried under reduced pressure, and recrystallized from n-hexane to obtain propranol Mole (TM) 230.8 g, yield 89.0%, purity 99.4%.

Embodiment 3

[0041] Add naphthol (I) (144.2g, 1mol), epichlorohydrin (113.3, 1.1mol), isopropylamine (90.5g, 1.5mol), tetrabutylammonium chloride (13.9g, 0.05mol) to In the reaction flask, lower the temperature to about 0°C, then slowly add 10% sodium hydroxide aqueous solution (400g) dropwise to the above reaction flask, after the addition, react at 0°C for 3h, then raise the temperature to 100°C and stir the reaction, TLC Monitoring, after 2 hours of reaction, lower the temperature to 0°C, add 10% sodium hydroxide aqueous solution (400g) dropwise, stir for 1 hour, filter, wash the filter cake with water and drain, dry under reduced pressure, and recrystallize from n-hexane to obtain propranolol ( TM) 228.2 g, yield 88.0%, purity 99.5%.

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Abstract

The invention discloses a preparation method for propranolol. The preparation method is characterized by comprising the following preparation steps: naphthol (I), epichlorohydrin and isopropylamine are used as initial raw materials, a reaction is performed under effects of a reaction solvent, an alkali and a phase transfer catalyst, and therefore the propranolol (TM) is obtained. According to thepreparation process, the reaction is finished in one step, thus the process steps are greatly simplified and easy to control, industrialized production can be realized, and process costs are reduced.

Description

technical field [0001] The invention belongs to the field of chemical medicine synthesis, and in particular relates to a preparation method of propranolol. Background technique [0002] Propranolol hydrochloride chemical name: 1-isopropylamino-3-(1-naphthyloxy)-2-propanol hydrochloride. Its structural formula is as follows: [0003] [0004] Propranolol hydrochloride is the first β-receptor blocker used in clinical practice, which can competitively inhibit the effect of catecholamine (catecholamine), and is often used to prevent and treat arrhythmia, angina pectoris, hypertension, myocardial infarction, coronary heart disease, and thyroid function Hypertension and other diseases, clinical application is extensive. In recent years, it has been found that the drug has many new uses, thereby expanding the scope of clinical application, mainly used for the treatment of sinus tachycardia, migraine, restless legs syndrome, mental diseases, and prevention of esophageal veins d...

Claims

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Application Information

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IPC IPC(8): C07C213/04C07C217/30
Inventor 曾培安刘达吴健民贺莲
Owner KAMP PHARMA
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