Improved preparation method of propranolol

A naphthyloxy and organic solvent technology, applied in the field of improved preparation of propranolol, can solve the problems of poor recovery effect, low recovery rate, easy loss and the like, and achieve the effects of less pollution, less side reactions, and less three wastes

Inactive Publication Date: 2015-02-18
HUAZHONG PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] The amination reaction of 3-(1-naphthyloxy)-1,2-epoxypropane and isopropylamine needs to use more than 3.5 times of isopropylamine, and needs to recycle isopropylamine after the reaction; It is easy to lose during the reaction process, the recovery effect is poor, and the recovery rate is low
There are certain disadvantages in industrial production

Method used

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  • Improved preparation method of propranolol
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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Weigh 200.2g of 3-(1-naphthyloxy)-1,2-propylene oxide, 70.9g of isopropylamine, Hβ molecular sieve (SiO 2 / Al 2 o 3 = 60) 4.0g and 1200ml of dichloromethane in a reaction flask. Stir the reaction at 30-35°C. The reaction was monitored by TLC. After 110 minutes, the reaction was stopped. The catalyst was removed by filtration, the filtrate was evaporated to dryness under reduced pressure, and the residue was recrystallized from n-hexane to obtain 239.4 g of propranolol with a yield of 92.3% and a purity of 99.2% by HPLC.

Embodiment 2

[0029] Weigh 200.2g of 3-(1-naphthyloxy)-1,2-propylene oxide, 76.8g of isopropylamine, Hβ molecular sieve (SiO 2 / Al 2 o 3 = 60) 2.0g and 1400ml of dichloromethane in a reaction flask. Stir the reaction at 25-30°C. The reaction was monitored by TLC. After 120 minutes, the reaction was stopped. The catalyst was removed by filtration, the filtrate was evaporated to dryness under reduced pressure, and the residue was recrystallized from n-hexane to obtain 241.2 g of propranolol with a yield of 93.0% and an HPLC purity of 99.1%.

Embodiment 3

[0031] Weigh 200.2 g of 3-(1-naphthyloxy)-1,2-propylene oxide, 59.1 g of isopropylamine, Hβ molecular sieve (SiO 2 / Al 2 o 3 = 60) 4.0g and 1200ml of dichloromethane in a reaction flask. Stir the reaction at 25-30°C. The reaction was monitored by TLC. After 130 minutes, the reaction was stopped. The catalyst was removed by filtration, the filtrate was evaporated to dryness under reduced pressure, and the residue was recrystallized from n-hexane to obtain 240.4 g of propranolol with a yield of 92.7% and an HPLC purity of 99.2%.

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Abstract

The invention discloses an improved preparation method of propranolol, which comprises the following step: in an organic solvent, 3-(1-naphthoxy)-1,2-propylene oxide reacts with isopropylamine under the action of a catalyst so as to obtain the propranolol. Compared with an existing preparation method, the method has the advantages that the preparation method is simple and convenient, reaction conditions are mild, the process is easy to control and the preparation method has small side effects; the catalyst has high catalytic activity and selectivity, is environmental-friendly and can be repeatedly used; a product is easy to separate and purify, the finished product with high purity can be obtained, yield is high, a small quantity of three wastes are generated, and the preparation method has low pollution and is suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of medicine and chemical industry, and in particular relates to an improved preparation method of propranolol. Background technique [0002] Propranolol hydrochloride is the first β-receptor blocker used clinically, and has made great contributions to the treatment of hypertension and angina pectoris. Scientist James Blake won the 1988 Nobel Prize in Medicine and the Queen's Award for this. [0003] Propranolol hydrochloride chemical name: 1-isopropylamino-3-(1-naphthyloxy)-2-propanol hydrochloride. The activity of the left-handed body is stronger than that of the right-handed body, and its racemic body is used clinically. Its structural formula is as follows: [0004] [0005] Propranolol hydrochloride is a commonly used clinical β-adrenoceptor blocker, which can competitively inhibit the effect of catecholamine (catecholamine), and is often used to prevent and treat arrhythmia, angina pectoris, hyper...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C217/30C07C213/04
Inventor 冯旋付林廖俊曾建华赵成安
Owner HUAZHONG PHARMA
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