Method for preparing 3-(2-aminopropyl)phenol

A technology of aminopropyl and phenol, which is applied in the field of preparation of 3-phenol, can solve the problems of complex post-processing operation, unfavorable industrial production, and poor production safety, so as to simplify the reaction process and post-processing process, reduce production risks, reduce The effect of production costs

Active Publication Date: 2017-05-10
SHANGHAI ZAIQI BIO TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] As reported in the follow-up comparative example (WO2009 / 68177A1), the total yield of the four-step reaction in the existing synthesis process is only 35.6%, and the raw material nitroethane used in the first step is a highly toxic and dangerous chemical; The second and third steps use sodium hydrogen and lithium aluminum tetrahydrogen respectively. These two reagents are not suitable for industrial production because they are flammable in contact with water, and the post-treatment operation is complicated; the fourth step uses palladium carbon, which is expensive.
On the whole, the existing synthesis process has the disadvantages of poor production safety, unfriendly to the environment, high production cost, and unfavorable for industrialized production

Method used

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  • Method for preparing 3-(2-aminopropyl)phenol

Examples

Experimental program
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Effect test

Embodiment 1

[0033] The first step: the synthesis of 1-(3-methoxyphenyl)isopropanol.

[0034] A solution of m-methoxybromobenzene (481mmol, 90g) in tetrahydrofuran (400ml) was slowly added dropwise to a solution of 1,2-dibromoethane (4ml) and magnesium chips (481mmol, 11.7g) in ether (400ml) , the reaction mixture was stirred and refluxed until the magnesium chips were dissolved. Propylene oxide (433mmol, 25.15g) was then added to the reaction mixture at 30°C, and the reaction was allowed to react at this temperature for 20 minutes, then the temperature was raised to room temperature and stirred for 1 hour. The reaction was quenched with aqueous ammonium chloride solution (600ml), and extracted with diethyl ether (2000ml), the organic layer was washed with water and brine successively, dried over sodium sulfate, spin-dried and cross-eluted column (eluent: petroleum ether / ethyl acetate= 4 / 1) 1-(3-methoxyphenyl)isopropanol (64.7g, yield: 80.89%) was obtained as an oily substance.

[0035] ...

Embodiment 2

[0049] The first step: the synthesis of 1-(3-methoxyphenyl)isopropanol.

[0050] A solution of m-methoxybromobenzene (481mmol, 90g) in ether (400ml) was slowly added dropwise to a solution of 1,2-dibromoethane (4ml) and magnesium chips (481mmol, 11.7g) in ether (400ml) , the reaction mixture was stirred and refluxed until the magnesium chips were dissolved. Then propylene oxide (457mmol, 26.5g) was added to the reaction mixture at 30°C, the reaction was allowed to react at this temperature for 20 minutes, then the temperature was raised to room temperature and stirred for 1 hour. The reaction was quenched with aqueous ammonium chloride solution (600ml), and extracted with diethyl ether (2000ml), the organic layer was washed with water and brine successively, dried over sodium sulfate, spin-dried and cross-eluted column (eluent: petroleum ether / ethyl acetate= 4 / 1) 1-(3-methoxyphenyl)isopropanol (65.6 g, yield: 82%) was obtained as an oily substance.

[0051] Through nuclear m...

Embodiment 3

[0063] The first step: the synthesis of 1-(3-methoxyphenyl)isopropanol.

[0064] A solution of m-methoxybromobenzene (481mmol, 90g) in 1,2-dibromoethane (400ml) was slowly added dropwise to 1,2-dibromoethane (4ml) and magnesium chips (481mmol, 11.7g) In a solution of diethyl ether (400ml), the reaction mixture was stirred at reflux until the magnesium chips were completely dissolved. Propylene oxide (409 mmol, 23.8 g) was then added to the reaction mixture at 30° C., the reaction was allowed to react at this temperature for 20 minutes, then the temperature was raised to room temperature and stirred for 1 hour. The reaction was quenched with aqueous ammonium chloride solution (600ml), and extracted with diethyl ether (2000ml), the organic layer was washed with water and brine successively, dried over sodium sulfate, spin-dried and cross-eluted column (eluent: petroleum ether / ethyl acetate= 4 / 1) 1-(3-methoxyphenyl)isopropanol (64.1 g, yield: 80.1%) was obtained as an oily subst...

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Abstract

The invention discloses a method for preparing 3-(2-aminopropyl)phenol. The method comprises the following steps: by taking m-bromoanisoles, epoxypropane, methanesulfonic acid, aminomethanol, hydrobromic acid and the like as raw materials, carrying out a four-step reaction, thereby obtaining the target product 3-(2-aminopropyl)phenol. The method disclosed by the invention is easy and convenient to operate and environmentally friendly, the comprehensive yield is 63% or higher and is obviously improved compared with the existing yield of 35.6%, the existing drug production cost is greatly reduced, and the method is suitable for large-scale industrial production.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a preparation method of 3-(2-aminopropyl)phenol. Background technique [0002] 3-(2-Aminopropyl)phenol, molecular formula C 9 h 13 NO, the molecular weight is 151.20, the English name is 3-(2-aminopropyl)phenol, it is an important pharmaceutical intermediate. [0003] As reported in the follow-up comparative example (WO2009 / 68177A1), the total yield of the four-step reaction in the existing synthesis process is only 35.6%, and the raw material nitroethane used in the first step is a highly toxic and dangerous chemical; The second and third steps use sodium hydrogen and lithium aluminum tetrahydrogen respectively. These two reagents are not suitable for use in industrial production because they are flammable in contact with water, and the post-processing operations are complicated; the fourth step uses palladium carbon, which is expensive. On the whole, the existi...

Claims

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Application Information

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IPC IPC(8): C07C41/30C07C43/23C07C303/28C07C309/66C07C213/02C07C217/60C07C213/08C07C215/52
CPCC07C41/30C07C213/02C07C213/08C07C303/28C07C43/23C07C309/66C07C217/60C07C215/52
Inventor 王治国宋艳红马秀娟田贝贝李世江李超李涛张欣
Owner SHANGHAI ZAIQI BIO TECH
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