Acebutolol synthesis

A technology of butyrylolol and synthetic method, which is applied in chemical instruments and methods, preparation of carboxylic acid amides, preparation of organic compounds, etc., can solve the problems of side reactions of ring-opening polymerization, difficulties in batch production, high cost, etc., and meet the reaction conditions Gentle, easy to operate, low cost effect

Inactive Publication Date: 2004-07-07
TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] The purpose of the present invention is to overcome the defect that epichlorohydrin in the prior art is prone to ring-opening polymerization side reactions under heating and reflux conditions, and to solve the problems of difficult batch production, low yield and high cost, etc., to provide a Synthesis method of butyrololol with mild reaction conditions at lower temperature, simple and convenient operation, high yield, low cost and suitable for industrial production

Method used

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  • Acebutolol synthesis

Examples

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Embodiment 1

[0024] (1) Synthesis of 5-butanylamino-2-(2,3-epoxypropoxy)acetophenone

[0025] At room temperature 19°C, in a 500ml container, dissolve 11g of solid sodium hydroxide in 150ml of water to obtain a sodium hydroxide solution; within 2 hours, under stirring, divide 5-butyrylamide-2-hydroxy The acetophenone solid was added into the sodium hydroxide solution, and the amount of each addition was 8 g, and the next batch of 5-butyrylamino-2-hydroxyacetophenone was added after each time it was dissolved. After the 5-butyrylamino-2-hydroxyacetophenone solid was completely dissolved in the sodium hydroxide solution, 42 g of epichlorohydrin was added dropwise to the reaction system, and stirring was continued after the addition was completed; after the reaction was carried out for 10 hours, additional solids were added 6g of sodium hydroxide, 21g of epichlorohydrin was added dropwise; after stirring for 10 hours, 6g of sodium hydroxide was added again, and 21g of epichlorohydrin was adde...

Embodiment 2

[0038] (1) Synthesis of 5-butanylamino-2-(2,3-epoxypropoxy)acetophenone

[0039] At room temperature 27°C, in a 500ml reactor, dissolve 23g of solid potassium hydroxide in 300ml of water to obtain an aqueous solution of potassium hydroxide; within 1 hour, under stirring, divide 5-butyrylamide-2- The hydroxyacetophenone solid is added in the potassium hydroxide solution, and the amount of each addition is 10 g, and the next batch of 5-butyrylamide-2-hydroxyacetophenone is added after each time it is dissolved. After the 5-butyrylamino-2-hydroxyacetophenone solid was completely dissolved in the potassium hydroxide solution, 25 g of epichlorohydrin was added dropwise to the reaction system, and stirring was continued after the addition was completed; after the reaction was carried out for 8 hours, additional 12g of solid potassium hydroxide, 13g of epichlorohydrin was added dropwise; after stirring for 8 hours, 12g of solid potassium hydroxide was added again, and 13g of epichlor...

Embodiment 3

[0045] (1) Synthesis of 5-butanylamino-2-(2,3-epoxypropoxy)acetophenone

[0046] At room temperature 14°C, in a 500ml container, dissolve 14g of solid sodium hydroxide in 250ml of water to obtain a sodium hydroxide solution; within 1 hour, under stirring, divide 5-butyrylamide-2-hydroxy The acetophenone solid is added in the sodium hydroxide solution, and the amount of each addition is 5 g, and the next batch of 5-butyrylamino-2-hydroxyacetophenone is added after each time it is dissolved. After the 5-butyrylamino-2-hydroxyacetophenone solid was completely dissolved in the sodium hydroxide solution, 44 g of epichlorohydrin was added dropwise to the reaction system, and stirring was continued after the addition was completed; after the reaction was carried out for 12 hours, additional solids were added 7g of sodium hydroxide, 22g of epichlorohydrin was added dropwise; after stirring for 12 hours, 7g of solid sodium hydroxide was added again, and 22g of epichlorohydrin was added...

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Abstract

A process for synthesizing sectral to treat cardiovascular and cerebrovascular diseases includes such steps as reacting between 5-butylamido-2-hydroxyphenyl ketone and epoxy chloropropane at 10-30 deg.C under existance of alkali solution to obtain 5-butylamido-2-(2,3-epoxypropoxy) phenyl ketone, and reacting on isopropane at 60-90 deg.C under existance of organic solvent. Its advantages are high output rate (60.5%) and low cost.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a synthesis method of the cardiovascular and cerebrovascular medicine aceterol. Background technique [0002] Acebutyrolol is a circulatory system drug, which has obvious curative effects on the treatment of hypertension, angina pectoris, antiarrhythmia, tachycardia and premature beats. [0003] The synthesis of propranolol is generally through a two-step reaction. First, under alkaline conditions, 5-butyrylamide-2-hydroxyacetophenone reacts with epichlorohydrin to generate 5-butyrylamide-2-(2,3 -glycidyloxy) acetophenone; then 5-butyrylamino-2-(2,3-epoxypropoxy) acetophenone reacts with isopropylamine to generate acetophenolol, the two-step reaction equation As follows: [0004] [0005] There have been related research reports on the synthesis of butyrololol through the above two-step reaction. In the first step reaction, U.S. Patent N...

Claims

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Application Information

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IPC IPC(8): C07C231/12C07C233/25
Inventor 王乃兴刘薇
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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