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Synthetic method of alprenolol drug intermediate allyl phenyl ether

A technique for the synthesis of allyl phenyl ether and the synthesis method, which is applied in the field of synthesis of allyl phenyl ether, the intermediate of alprenolol, can solve the problems of non-inhibition of myocardial contractility and membrane-free stability, and achieve The effect of reducing reaction temperature and reaction time, reducing intermediate links, and increasing reaction yield

Inactive Publication Date: 2016-04-13
CHENGDU KA DI FU TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

No endogenous sympathomimetic activity, no membrane stability, no inhibitory effect on myocardial contractility

Method used

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  • Synthetic method of alprenolol drug intermediate allyl phenyl ether

Examples

Experimental program
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Effect test

example 1

[0011] In the reaction vessel equipped with stirrer, thermometer and reflux condenser, add phenol (2) 0.6mol, allylamine (3) 0.65mol, sodium sulfite 0.71mol, mass fraction is 70% xylene 230ml, control the stirring speed At 160rpm, the temperature of the solution was raised to 80°C, refluxed for 5h, poured into 800ml mass fraction of 15% sodium chloride solution after cooling, the aqueous layer was extracted 3 times with 65% cyclohexanone, and the organic layer and cyclohexanone were combined. Hexanone extract, washed with 35% sodium bisulfite solution, dehydrated with anhydrous calcium sulfate, distilled to remove cyclohexanone, distilled under reduced pressure at 1.21kPa, collected fractions at 70--76°C to obtain allylbenzene Base ether 66.73g, yield 83%.

example 2

[0013] In the reaction vessel equipped with stirrer, thermometer and reflux condenser, add phenol (2) 0.6mol, allylamine (3) 0.67mol, sodium sulfite 0.73mol, mass fraction is 72% xylene 230ml, control the stirring speed At 170rpm, the temperature of the solution was raised to 82°C, refluxed for 6h, poured into 800ml mass fraction of 17% sodium chloride solution after cooling, the aqueous layer was extracted 4 times with 67% cyclohexanone, and the organic layer and ring Hexanone extract, washed with 37% sodium bisulfite solution, dehydrated with solid sodium hydroxide, distilled off cyclohexanone, distilled under reduced pressure at 1.22kPa, collected fractions at 70--76°C to obtain allylbenzene Base ether 69.95g, yield 87%.

example 3

[0015] In the reaction vessel equipped with stirrer, thermometer and reflux condenser, add phenol (2) 0.6mol, allylamine (3) 0.68mol, sodium sulfite 0.76mol, mass fraction is 75% xylene 230ml, control the stirring speed At 190rpm, the temperature of the solution was raised to 85°C, refluxed for 7h, poured into 800ml mass fraction of 20% sodium chloride solution after cooling, the aqueous layer was extracted 5 times with 70% cyclohexanone, and the organic layer and cyclohexanone were combined. Hexanone extract, washed with 40% sodium bisulfite solution, dehydrated with anhydrous calcium sulfate, distilled to remove cyclohexanone, distilled under reduced pressure at 1.23kPa, collected fractions at 70--76°C to obtain allylbenzene Base ether 73.16g, yield 91%.

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Abstract

A synthetic method of an alprenolol drug intermediate of allyl phenyl ether comprises the following steps: adding 0.6mol of phenol, 0.65-0.68mol of allyl amine, 0.71-0.76mol of sodium sulfite and 230ml of xylene into a reaction container provided with a stirrer, a thermometer and a reflux condenser, controlling a stirring speed at 160-190rpm, raising solvent temperature to 80-85 DEG C, refluxing for 5-7h, after cooling, pouring into 800ml of sodium chloride solvent, extracting a water layer with cyclohexanone for 3-5 times, combining an organic layer and a cyclohexanone extracted solvent, washing with a sodium hydrogen sulfite solvent, dehydrating with a dehydrating agent, evaporating to move the cyclohexanone, distilling under reduced pressure, and collecting a fraction of 70-76 DEG C to obtain the allyl phenyl ether, wherein the mass percent of the xylene in the step is 70-75%, the mass percent of the sodium chloride solvent in the step is 15-20%, and the mass percent of the cyclohexanone in the step is 65-70%.

Description

technical field [0001] The invention relates to a method for synthesizing alprenolol drug intermediate allyl phenyl ether. Background technique [0002] Alprenolol drugs competitively inhibit catecholamines at the adrenergic beta receptor site. By weakening or preventing the excitation of β receptors, the contraction force and contraction velocity of the heart are reduced, and the conduction velocity through the conduction system is slowed down, so that the heart's response to exercise or stress is weakened. Therefore, it is used in the treatment of angina pectoris to reduce myocardial oxygen consumption and increase exercise tolerance. It is used in the treatment of arrhythmias because it blocks the adrenergic excitation of the cardiac pacemaker potential. It is possible that this product lowers blood pressure through central, adrenergic neuron blockade, anti-renin activity, and reduced cardiac output, and is suitable for the treatment of hypertension. Because this produ...

Claims

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Application Information

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IPC IPC(8): C07C41/01C07C41/34C07C41/42C07C43/205
CPCC07C41/01C07C41/34C07C41/42
Inventor 廖如佴
Owner CHENGDU KA DI FU TECH