Synthetic method of 2-thiophene ethylamine

A technology of thienylethylamine and its synthesis method, which is applied in the fields of medicine and chemical industry, can solve the problems of 2-thienylethylamine product handling, cumbersome product post-processing, a large amount of waste water and waste acid, etc., achieve mild reaction conditions and reduce production costs , the effect of high total yield

Active Publication Date: 2013-10-16
ZHEJIANG LIAOYUAN PHARM CO LTD
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Problems solved by technology

This method synthesizes 2-thiopheneethylamine, the reaction conditions are mild, the product yield is higher, and it is more suitable for industrial production, but the product post-treatment is more loaded down with trivial details, a large amount of waste water and waste acid are produced in the reaction, and the environmental pollution is relatively serious; Chinese national knowledge The website of the Intellectual Property Office also...

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  • Synthetic method of 2-thiophene ethylamine

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Embodiment 1

[0026] Embodiment 1: the preparation of esterification product:

[0027] Add 35.0g (0.184mol) p-toluenesulfonyl chloride and 45ml toluene to a 250ml four-neck flask equipped with a drying tube at room temperature, stir and dissolve, then add 22.5g (0.176mol) thiophene ethanol, cool to 0-5°C, Add 8.5g (0.213mol) of sodium hydroxide, stir and react at 0-5°C for 5 hours, suction filter after the reaction, rinse the filter cake with 30ml of toluene, and drain to obtain a wet product of solid sodium chloride and sodium hydroxide at about 12.9 g. The filtrate was decompressed to remove toluene, until there was no flow, and then distilled under reduced pressure for 30 minutes to obtain 49.8 g of sulfonic acid ester concentrate. The high performance liquid chromatography (HPLC) analysis showed that the content of sulfonic acid ester was 99.4%, and the yield was 99%. .

Embodiment 2

[0028] Embodiment 2: the preparation of esterification product:

[0029] Add 35.0g (0.184mol) p-toluenesulfonyl chloride and 45ml toluene to a 250ml four-neck flask equipped with a drying tube at room temperature, stir and dissolve, then add 22.5g (0.176mol) thiophene ethanol, cool to 0-5°C, Add 14.4g (0.360mol) of sodium hydroxide, stir and react at 0-5°C for 5 hours, filter with suction after the reaction, rinse the filter cake with 30ml of toluene, and drain to obtain a wet product of solid sodium chloride and sodium hydroxide of about 20.1 g. The filtrate was decompressed to remove toluene, until there was no flow, and then distilled under reduced pressure for 30 minutes to obtain 50.0 g of sulfonic acid ester concentrate. The high performance liquid chromatography (HPLC) analysis showed that the content of sulfonic acid ester was 99.0%, and the yield was 99%. .

Embodiment 3

[0030] Embodiment 3: the preparation of esterification product:

[0031] Add 35.0g (0.184mol) p-toluenesulfonyl chloride and 45ml toluene to a 250ml four-necked flask equipped with a drying tube at room temperature, stir and dissolve, add 22.5g (0.176mol) thiophenethanol, and add 8.5g ( 0.213mol) sodium hydroxide, stirred and reacted at 25°C for 5 hours, suction filtered after the reaction, the filter cake was rinsed with 30ml of toluene, and dried to obtain about 12.9g of wet solid sodium chloride and sodium hydroxide. The filtrate was decompressed to remove toluene, until there was no flow, and then distilled under reduced pressure for 30 minutes to obtain 49.6 g of sulfonic acid ester concentrate. The high performance liquid chromatography (HPLC) analysis showed that the content of sulfonic acid ester was 98.6%, and the yield was 98%. .

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Abstract

The invention provides a synthetic method of 2-thiophene ethylamine. The synthetic method is characterized in that: the 2-thiophene ethylamine is obtained through esterification, ammonification and dissociation in non-aqueous medium by using 2-thiopheneethanol as initial raw materials. The synthetic method comprises the following steps of: (1) an esterification reaction, i.e., generating an esterified substance under the condition of solid base catalysis from 2-thiopheneethanol and p-toluenesulfonyl chloride in an organic solvent; (2) an ammonification reaction, i.e., injecting liquid ammonia into the esterified substance, pressurizing and ammonifying so as to generate 2-thienylethamino-4-toluenesulfonate; (3) a dissociation reaction, i.e., reacting the 2-thienylethamino-4-toluenesulfonate with a solid base in the organic solvent by the dissociation so as to prepare the 2-thiophene ethylamine. The whole preparation process of the 2-thiophene ethylamine is completed in the non-aqueous medium so that no waste water is discharged, solid waste materials are recycled and reused, and the purpose of green production is achieved. Besides, reaction conditions are milder, post treatment process is simpler, yield is high, and industrial production is facilitated.

Description

technical field [0001] The invention belongs to the technical field of medicine and chemical industry, in particular to a method for synthesizing 2-thienylethylamine. Background technique [0002] 2-Thienylethylamine can be used in the synthesis of various drugs. It is a key drug intermediate for the preparation of various cardiovascular diseases related to platelets and thrombus and new drugs for anti-inflammatory and analgesic. The drugs ticlopidine hydrochloride, clopidogrel bisulfate, and prasugrel hydrochloride. With the continuous development of its downstream products, the prospect of 2-thienylethylamine and its derivatives will be broader. [0003] There are many research reports on the synthesis process of 2-thiopheneethylamine. Among them, there are four synthetic routes for industrialization or industrial application prospects. The specific synthesis process is as follows: 1. Nitromethane method: This method is to combine thiophene and N,N -Dimethylformamide (DM...

Claims

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Application Information

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IPC IPC(8): C07D333/20
Inventor 胡华南李浙东司磊华莹屠雄飞杨敏华
Owner ZHEJIANG LIAOYUAN PHARM CO LTD
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