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Ethyl 3-(pyridin-2-ylamino)propanoate post-treatment purification method

A technology of ethyl propionate and purification method, which is applied in the field of compound purification and post-processing and purification of 3-ethyl propionate, can solve the problems of complicated post-processing process, low yield, unenvironmental protection, etc., and achieve technological progress Significant, improved purity, low production cost effects

Inactive Publication Date: 2015-09-16
SHANGHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] Aiming at the above-mentioned technical problems in the prior art, the invention provides a kind of aftertreatment purification method of ethyl 3-(pyridin-2-ylamino)propionate, described this 3-(pyridin-2-ylamino ) The post-treatment purification method of ethyl propionate solves the complex post-treatment process of 3-(pyridin-2-ylamino) ethyl propionate in the prior art, and involves the use of toxic drugs, is uneconomical, not environmentally friendly, and has a high yield. low rate technical issues

Method used

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  • Ethyl 3-(pyridin-2-ylamino)propanoate post-treatment purification method
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  • Ethyl 3-(pyridin-2-ylamino)propanoate post-treatment purification method

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Embodiment 1

[0028] This example dabigatran etexilate synthetic process intermediate 3-(pyridin-2-yl amino) ethyl propionate is synthetic, and described synthetic reaction equation is as follows:

[0029]

[0030] The synthetic concrete steps of above-mentioned reaction and aftertreatment purification method are as follows:

[0031] (1) Take a 500mL round-bottomed flask, put it into an electromagnetic stirrer of appropriate size, weigh 50g of o-aminopyridine into the bottle, and add 28.3mL of absolute ethanol;

[0032] (2) Stir for 20 minutes, and when the solid is dissolved or mostly dissolved, add 56.5 mL of ethyl acrylate to step (1);

[0033] (3) Stir for 10min, slowly add 4.8mL trifluoromethanesulfonic acid dropwise;

[0034] (4) Add nitrogen protection, stir and reflux in an oil bath at 120-160°C for 16-20 hours;

[0035] (5) After the reaction is completed, the reaction solution is washed with recovered petroleum ether or ethyl acetate for 2 to 3 times at a temperature of 35-40...

Embodiment 2

[0041] This example dabigatran etexilate synthetic process intermediate 3-(pyridin-2-yl amino) ethyl propionate is synthetic, and described synthetic reaction equation is as follows:

[0042]

[0043] The synthetic concrete steps of above-mentioned reaction and aftertreatment purification method are as follows:

[0044] (1) Take a 500mL round-bottomed flask, put it into an electromagnetic stirrer of appropriate size, weigh 100g of o-aminopyridine into the bottle, and add 56.6mL of absolute ethanol;

[0045] (2) Stir for 20 minutes, and when the solid is dissolved or most of it is dissolved, add 113 mL of ethyl acrylate to step (1);

[0046] (3) Stir for 10 min, slowly add 9.6 mL of trifluoromethanesulfonic acid dropwise;

[0047] (4) Add nitrogen protection, stir and reflux in an oil bath at 120-160°C for 16-20 hours;

[0048] (5) After the reaction is completed, the reaction solution is washed with recovered petroleum ether or ethyl acetate for 2 to 3 times at a temperat...

Embodiment 3

[0054] This example dabigatran etexilate synthetic process intermediate 3-(pyridin-2-yl amino) ethyl propionate is synthetic, and described synthetic reaction equation is as follows:

[0055]

[0056] The synthetic concrete steps of above-mentioned reaction and aftertreatment purification method are as follows:

[0057] (1) Take a 500mL round-bottomed flask, put it into an electromagnetic stirrer of appropriate size, weigh 150g of o-aminopyridine into the bottle, and add 84.9mL of absolute ethanol;

[0058] (2) Stir for 20 minutes, and when the solid is dissolved or mostly dissolved, add 169.5 mL of ethyl acrylate to step (1);

[0059] (3) Stir for 10 min, slowly add 14.4 mL of trifluoromethanesulfonic acid dropwise;

[0060](4) Add nitrogen protection, stir and reflux in an oil bath at 120-160°C for 16-20 hours;

[0061] (5) After the reaction is completed, the reaction solution is washed with recovered petroleum ether or ethyl acetate for 2 to 3 times at a temperature o...

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Abstract

The invention relates to an ethyl 3-(pyridin-2-ylamino)propanoate post-treatment purification method, which comprises: adding a first organic solvent to a reaction mother liquid, adding silica gel to carry out stirring adsorption, adding a second organic solvent to carry out elution, carrying out pressure reducing concentration on the eluent to obtain a target compound, and re-crystallizing with a third organic solvent to obtain the white flaky crystal, ie., ethyl 3-(pyridin-2-ylamino)propanoate. According to the present invention, the method adopts the silica gel adsorption and the re-crystallizing, the pigment and the by-product generated in the reaction are removed, the purity of the organic target product is improved, and the high purity target compound is obtained.

Description

technical field [0001] The invention belongs to the field of chemical industry, and in particular relates to a method for purifying a compound, in particular to a method for post-processing and purifying ethyl 3-(pyridin-2-ylamino)propionate. Background technique [0002] Ethyl 3-(pyridin-2-ylamino)propionate (compound 1) is one of the important intermediates in the synthesis of the direct thrombin inhibitor dabigatran etexilate (dabigatrau etexilate, trade name Pradaxa, compound 2) . [0003] [0004] In the prior art, for example, the synthetic route of ethyl 3-(pyridin-2-ylamino)propionate is shown in formula 1: [0005] [0006] The method is to first synthesize 2-chloropyridine N-oxide (yield 87%) and β-alanine ethyl ester hydrochloride (yield: 93%); then by 2-chloropyridine N-oxide and β - Ethyl aminopropionate hydrochloride reacts to generate 3-(pyridin-2-ylamino) ethyl propionate N-oxide (yield: 70%); finally generates 3-(pyridine- 2-ylamino) ethyl propionat...

Claims

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Application Information

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IPC IPC(8): C07D213/74
CPCC07D213/74
Inventor 任玉杰王飞
Owner SHANGHAI INST OF TECH
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