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Method for synthesizing beta-suprarenal kinetin ractopamine hydroc hloride

A technology of ractopamine and synthesis method, applied in chemical instruments and methods, preparation of organic compounds, preparation of aminohydroxy compounds, etc., can solve the problem of long synthesis route of ractopamine, low yield of final product hydrochloride, and yield of intermediate products. Low problems, to achieve the effect of cheap raw materials, simple equipment and operation, and less by-products

Inactive Publication Date: 2013-04-17
NORTH CHINA UNIV OF WATER RESOURCES & ELECTRIC POWER
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0014] In summary, the synthetic route of ractopamine disclosed by U.S. Eli Lilly (Eli Lilly) company is longer, with more by-products and higher cost; the patent route with publication number CN1116620 has been improved, and the raw material is cheap and easy to get, but there are Obvious deficiencies, more expensive as solvent tetrahydrofuran (THF) market price, long-term storage can produce peroxide; Intermediate product yield is low, only has 73%~82%; Yield is also relatively low, only 75%~90%, utilize metal borohydride to obtain the free base of final product in aqueous phase, cause the hydrochloride yield of final product very low, only have about 65%, and will bring serious pollution

Method used

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  • Method for synthesizing beta-suprarenal kinetin ractopamine hydroc hloride
  • Method for synthesizing beta-suprarenal kinetin ractopamine hydroc hloride
  • Method for synthesizing beta-suprarenal kinetin ractopamine hydroc hloride

Examples

Experimental program
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Effect test

example 1

[0051] Example 1: The synthetic method of β-adrenergic hormone ractopamine, comprises the following steps:

[0052] (1) Add 20g of p-hydroxyacetophenone, 50mL of benzene and 100mL of saturated sodium carbonate aqueous solution into a 500mL three-necked flask, heat to 50°C, slowly add 24mL of benzoyl chloride dropwise, and then raise the temperature and reflux at 40-90°C for 2 hours , and distill out benzene at the same time; then slowly heat 50mL of water, continue heating and distilling to steam temperature of 90°C, cool, white crystals are precipitated, filter with suction, wash the filter cake with water until neutral, and dry to obtain esterified benzoic acid (4 -Acetophenyl) ester 35.12 g. The yield of this step is 99.5%.

[0053] (2) Add 30 g of the above-mentioned esterified product and 150 mL of carbon tetrachloride into a 500 mL three-neck flask, heat up to 40°C, slowly add 12 mL of liquid bromine dropwise, then slowly heat up and reflux for 2 hours, cool to obtain w...

example 2

[0058] Example 2: The synthetic method of β-adrenergic hormone ractopamine, comprises the following steps:

[0059] (1) In a 250mL three-necked flask, add 10g of p-hydroxyacetophenone, 25mL of toluene and 50mL of 15% aqueous sodium hydroxide solution, heat to 40°C, slowly add 12mL of benzoyl chloride dropwise, and heat up to reflux for 3h after the dropwise addition, Distill out toluene, then slowly heat 25mL of water, continue to heat and distill until the steam temperature is 90°C, after the reaction is completed, cool, and white crystals are precipitated, filter with suction, wash the filter cake with water until neutral, and dry to obtain 17.47g of esterified product. The yield of this step is 99%.

[0060] (2) Add 15g of the above-mentioned esterified product and 80mL of chloroform into a 250mL three-necked flask, heat up to 60°C, slowly add 8mL of liquid bromine dropwise, then slowly heat up and reflux for 1.5h, cool to obtain white crystals, suction filter, wash, and dr...

example 3

[0065] Example 3: The synthetic method of β-adrenergic hormone ractopamine, comprises the following steps:

[0066] (1) In a 500mL three-neck flask, add 25g of p-hydroxyacetophenone, 50mL of benzene and 100mL of saturated aqueous sodium carbonate solution, heat to 80°C, slowly add 28mL of benzoyl chloride dropwise, after the dropwise addition, heat up and reflux for 2.5h, while distilling Benzene was released; then slowly heated 60mL of water, continued heating and distillation until the steam temperature was 90°C, cooled, white crystals were precipitated, filtered with suction, washed the filter cake with water until neutral, and dried to obtain 43.45g of esterified product. The yield of this step is 98.5%.

[0067] (2) Add 40g of the above-mentioned esterified product and 200mL of carbon tetrachloride into a 500mL three-necked flask, heat up to 80°C, slowly add 20mL of liquid bromine dropwise, and then slowly heat up and reflux for 3 hours; cool to obtain white crystals, suc...

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Abstract

The invention discloses a method for synthesizing beta-suprarenal kinetin ractopamine hydroc hloride. The method comprises the following steps of: reacting hydroxyacetophenone with acyl chloride under the alkali condition to obtain the esters: benzoic acid(4-acetylphenyl)ester; reacting the obtained ester with bromine to obtain the bromides; reacting raspberry ketone, ammonia gas and hydrogen gasto obtain amides; reacting the bromides with amides to obtain the condensation product: benzoic acid[1-methyl-3-(4-hydroxyphenyl)-propylamino]-acetophenone ester; dissolving the condensation product in the mixture of hydrochloric acid and alcohol to obtain hydrolysates; and performing catalytic hydrogenation on the hydrolysates to obtain the finished product ractopamine hydroc hloride. By the method, the yield is high, byproducts are reduced, the purity is high, the ractopamine hydroc hloride content of finished products is over 93 percent, raw materials are low in cost and readily available,the reaction conditions are mild, energy consumption is low, emission of 'three wastes' (waste gas, waste water and waste residues) is avoided, the method is environmentally-friendly, the equipment and operation are simple, and the method is applicable for industrial production.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry and relates to a method for synthesizing the drug β-adrenergic hormone ractopamine. Background technique [0002] The molecular formula of ractopamine (English name Ractopamine hydroc hloride) is C 18 h 23 NO 3 , the molecular formula of its hydrochloride is C 18 h 23 NO 3 HCl, chemical name: 1-(4-hydroxyphenyl)-2-[1-methyl-3-(4-hydroxyphenyl)propylamino]-ethanol hydrochloride, its structure is as follows: [0003] [0004] Ractopamine hydrochloride, trade name Paylean (Paylean), was researched and developed by Eli Lilly (Eli Lilly) in 1999. It is a class of phenylethanolamine derivatives similar in structure and function to adrenaline and norepinephrine. It was certified by the US Food and Drug Administration (FDA) that year, and it is a high-tech product. Its (R, R)-optical isomer has strong biological activity and can be used as a cardiotonic drug in medicine for the treatment of co...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C215/60C07C213/00
Inventor 王海荣李国亭刘秉涛杨光瑞闫金霞
Owner NORTH CHINA UNIV OF WATER RESOURCES & ELECTRIC POWER
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