Novel propranolol synthesis method

A new method and naphthyloxy technology, applied in the field of synthesizing propranolol, can solve the problems of low recovery rate, poor recovery effect, easy loss, etc., and achieve the effects of less side reactions, less pollution, and less three wastes

Inactive Publication Date: 2015-10-07
HUAZHONG PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] The ring-opening reaction of 3-(1-naphthyloxy)-1,2-epoxypropane and isopropylamine has a yield of only about 50%, and usually needs to use more than 3.5 times of isopropylamine, and needs to recover isopropylamine after the reaction; And isopropylamine boiling point is lower, loses easily in reaction process, and recovery effect is poor, and recovery rate is low
There are certain disadvantages in industrial production

Method used

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Weigh 200.2 g of 3-(1-naphthyloxy)-1,2-propylene oxide, 70.9 g of isopropylamine and 1800 ml of dichloromethane, and place them in a reaction flask. With the temperature controlled below 30°C, 4.0 g of triethylamine was slowly added dropwise with stirring. After dropping, keep warm at 25-30°C and stir for reaction. The reaction was monitored by TLC. After 5 hours, the reaction was stopped. The residue was evaporated to dryness under reduced pressure, and the residue was recrystallized from toluene / n-hexane to obtain 243.3 g of propranolol, with a yield of 93.8% and an HPLC purity of 99.3%.

Embodiment 2

[0027] Weigh 200.2 g of 3-(1-naphthyloxy)-1,2-propylene oxide, 76.8 g of isopropylamine and 1000 ml of dichloromethane, and place them in a reaction flask. With the temperature controlled below 30°C, 2.3 g of triethylamine was slowly added dropwise with stirring. After dropping, keep warm at 25-30°C and stir for reaction. The reaction was monitored by TLC. After 5.5 hours, the reaction was stopped. The residue was evaporated to dryness under reduced pressure, and the residue was recrystallized from toluene / n-hexane to obtain 244.0 g of propranolol, with a yield of 94.1% and an HPLC purity of 99.2%.

Embodiment 3

[0029] Weigh 200.2 g of 3-(1-naphthyloxy)-1,2-propylene oxide, 59.1 g of isopropylamine and 1600 ml of dichloromethane, and place them in a reaction flask. With the temperature controlled below 30°C, 2.5 g of triethylamine was slowly added dropwise with stirring. After dropping, keep warm at 25-30°C and stir for reaction. The reaction was monitored by TLC. After 6 hours, the reaction was stopped. The residue was evaporated to dryness under reduced pressure, and the residue was recrystallized from toluene / n-hexane to obtain 241.2 g of propranolol, with a yield of 93.0% and an HPLC purity of 99.1%.

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Abstract

The invention discloses a novel propranolol synthesis method. The method includes the following steps that 3-(1-naphthoxy)-1, 2-epoxypropane and isopropylamine generate a ring-opening reaction in the presence of a catalyst, propranolol is obtained, the yield is larger than or equal to 93%, and the purity is larger than or equal to 99%. Compared with an existing preparation method, the method has the advantages that the method is easy and convenient to implement, the reaction condition is mild, the catalytic activity and selectivity of the catalyst are high, few side reactions happen, products can be separated and purified easily, less device corrosion and less pollution to the environment are caused, end products with the high purity can be obtained, the yield is high, and the method 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 a new method for synthesizing 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, hypertens...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C217/30C07C213/04
Inventor 冯旋付林廖俊魏旭力王勇
Owner HUAZHONG PHARMA
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