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Synthetic method of 2-thiophene ethylamine

A technology of thienylethylamine and its synthetic method, applied in the direction of organic chemistry, etc.

Inactive Publication Date: 2013-09-11
TAIYUAN UNIV OF TECH
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Problems solved by technology

Chinese invention patent CN101885720A has disclosed "a kind of synthetic method of 2-thiopheneethylamine", the synthetic method is from 2-bromothiophene → 2-thiophene ethanol → 2-thiophene benzene sulfonate → 2-thiopheneethylamine, its existing The disadvantage is that the used benzenesulfonyl chloride is seriously polluted
The disadvantage of this method is that the dissolved ammonia in isopropanol is volatile and needs to be reacted at a pressure of 20 bar, and the catalyst Raney Ni is difficult to regenerate

Method used

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  • Synthetic method of 2-thiophene ethylamine

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Embodiment 1

[0029] 1) PCC / SiO2 2 Preparation of oxidizing agent

[0030] Under stirring, 20g (0.2mol) CrO 3 Add it to 38.8mL (6mol / L) hydrochloric acid, cool the homogeneous system to 0°C after 5min, slowly add 15.8g (0.2mol) pyridine dropwise, and precipitate occurs. After adding, continue to react for 1h and filter. Add 140mL of water to the filter cake until the solids are completely dissolved, add 100g of macroporous silica gel (pore size 400-500?) at 50°C and impregnate for 24h. Vacuum drying for 24 h yielded 143 g of product.

[0031] 2) Preparation of 2-thiopheneacetaldehyde

[0032] 143g PCC / SiO 2 1. Add 500mL of n-hexane into the reaction flask, heat to 50°C, and slowly drop in a solution consisting of 12.8g of 2-thiophenethanol and 30mL of n-hexane. After dropping, it was detected by TLC until the conversion of the reaction raw materials was completed. Filter, wash the filtrate three times with water, and concentrate to obtain 2-thiopheneacetaldehyde.

[0033] 3) Prepa...

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Abstract

The invention discloses a synthetic method of 2-thiophene ethylamine. The method comprises the steps of oxidizing 2-thiophene ethanol to obtain 2-thiophene aldehyde by loaded pyridinium chlorochromate (PCC / SiO2), enabling the 2-thiophene aldehyde to react with hydroxylamine hydrochloride to obtain 2-thiophene acetaldehyde oxime; and reducing the 2-thiophene acetaldehyde oxime to obtain the 2-thiophene ethylamine through an NaBH4 / CuSO4 / Amberlyst-15 system. The method disclosed by the invention is mild in reaction condition, high in yield, small in pollution and suitable for industrialized production.

Description

technical field [0001] The invention relates to a synthesis method of 2-thienylethylamine, in particular to a method for preparing 2-thienylethylamine through oxidation, hydroxylation and reduction of 2-thiophenethanol as a raw material. Background technique [0002] 2-Thienylethylamine can be used to synthesize various drugs such as clopidogrel and prasugrel, and people have carried out in-depth research on its synthesis. Chinese invention patent CN101885720A has disclosed "a kind of synthesis method of 2-thiopheneethylamine". The disadvantage is that the used benzenesulfonyl chloride is seriously polluted. Fine Chemical Industry, 2001,18(1):53-55 reported "the synthesis of 2-thiopheneethylamine", using 2-thiophene formaldehyde → 2-thiophene acetaldehyde → 2-thiophene acetaldehyde oxime → 2-thiophene ethylamine The synthetic route of this method, the total yield of this method is 27.2%, and yield is on the low side. Guangxi Chemical Industry, 2001,30(2):15-16 reported "t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/20
Inventor 邢俊德张朝峰张照昱李瑜魏文珑常宏宏李兴
Owner TAIYUAN UNIV OF TECH
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