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Method for synthesizing 2-thienyl ethylamine by means of biological catalysis

A technology of thienylethylamine and biocatalysis, which is applied in the fields of chemical industry and medicine, can solve the problems of high cost of chemical synthesis technology, and achieve the effects of environmental friendliness, cost reduction and mild reaction conditions

Active Publication Date: 2017-07-14
TAIYUAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The object of the present invention is to aim at the deficiency of the high cost of existing chemical synthesis technology, to provide a kind of synthesis method with mild reaction conditions, simple operation, high yield and low cost, especially using microorganisms with almost no environmental pollution to convert 2-nitro The synthetic method of reducing vinylthiophene to 2-thienylethylamine

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Dissolve 3 g of glucose, 0.7 g of disodium hydrogen phosphate and 0.6 g of potassium dihydrogen phosphate in 100 mL of water, adjust the pH to 8, sterilize for 30 min, and cool to obtain a culture medium for Bacillus licheniformis;

[0021] Add 10 g of Bacillus licheniformis to the above medium, and activate it for 1 hour in a shaker at a speed of 180 rpm and a constant temperature of 37°C.

[0022] Dissolve 0.5 g of 2-nitrovinylthiophene in 5 mL of tetrahydrofuran, then add it to the activated medium solution, and biocatalyze the reaction at 37 °C for 96 hours in a shaker with a rotation speed of 180 rpm. During the reaction, keep pH=8, after the reaction, the reaction solution was centrifuged, the supernatant was extracted with ethyl acetate, washed with saturated brine, dried over anhydrous sodium sulfate, and distilled under reduced pressure to obtain the product 2-thiopheneethylamine with a yield of 75.5%.

Embodiment 2

[0024] Activation and reuse of Bacillus licheniformis

[0025] Dissolve 3 g of glucose, 0.7 g of disodium hydrogen phosphate and 0.6 g of potassium dihydrogen phosphate in 100 mL of water, adjust the pH to 8, sterilize for 30 min, and cool to obtain a culture medium for Bacillus licheniformis;

[0026] Add 15 g of Bacillus wetlicheniformis obtained by centrifugation in Example 1 to the above-mentioned medium, then add a solution consisting of 0.5 g of 2-nitrovinylthiophene and 5 mL of tetrahydrofuran, and place in a shaker at 37°C with a rotation speed of 180 rpm Biocatalytic reaction per minute for 96 hours, keep pH=8 during the reaction, centrifuge the reaction liquid after the reaction, extract the supernatant with ethyl acetate solvent, wash with saturated saline, dry over anhydrous sodium sulfate, and distill under reduced pressure to obtain the product 2- Thiphenethylamine, the yield is 73.0%.

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Abstract

The invention relates to a method for synthesizing 2-thienyl ethylamine by means of biological catalysis. The method comprises the steps of preparing glucose, disodium hydrogen phosphate and potassium dihydrogen phosphate into a water solution according to a certain proportion, sterilizing and cooling to obtain a bacillus licheniformis culture medium; activating the obtained bacillus licheniformis culture medium in a shaking table at the constant temperature according to a certain cell concentration; then, dissolving 2-nitro vinyl thiophene, adding the solution into the activated culture medium, carrying out a biological catalysis reaction, and then carrying out centrifugal separation; extracting supernatant by using ethyl acetate, washing, drying, and carrying out reduced pressure distillation to obtain the product 2-thienyl ethylamine. The method has the remarkable characteristics and progress of being simple in technology, high in synthetic yield, low in cost and less in environmental pollution.

Description

technical field [0001] The invention relates to a method for synthesizing 2-thiopheneethylamine, in particular to a method for synthesizing 2-thiopheneethylamine by biocatalytic reduction of 2-nitrovinylthiophene with Bacillus licheniformis, belonging to the technical fields of chemical industry and medicine. Background technique [0002] 2-Thienylethylamine is an important intermediate for the synthesis of ticlopyridine hydrochloride, a drug for cardiovascular and cerebrovascular diseases. Drugs and other bioactive drug intermediates. The most common synthesis method reported in the literature is to use thiophene as a raw material to prepare 2-thiophenecarbaldehyde, then react with nitromethane to obtain 2-nitrovinylthiophene, and finally obtain 2-thiopheneethylamine through reduction. In this designed synthetic route, the last step of the reduction reaction requires the reduction of both the double bond and the nitro group, and the molecule contains sulfur, resulting in h...

Claims

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Application Information

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IPC IPC(8): C12P17/00C12N1/20C12R1/10
CPCC12N1/20C12P17/00
Inventor 秦育红邢俊德范晓军朱国峰孙权威冯敏敏
Owner TAIYUAN UNIV OF TECH
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