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Synthesis method of 4,5,6,7-tetrahydrothieno[3,2-c]pyridine hydrochloride

A technology of pyridine hydrochloride and tetrahydrothiophene, applied in the direction of organic chemistry and the like, can solve the problems of difficult preparation, high toxicity and high cost of 2-thiopheneethylamine, and achieve the effects of high yield, simplified synthesis process and environmental friendliness

Inactive Publication Date: 2017-08-18
TAIYUAN UNIV OF TECH +1
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Problems solved by technology

[0013] The weak points of these methods: (1) raw material 2-thienylethylamine is difficult to prepare, and the price is high, resulting in higher cost of product 4,5,6,7-tetrahydrothiophene[3,2-c]pyridine hydrochloride ;(2) To use highly toxic and carcinogenic formaldehyde during preparation, which seriously affects the health of operators

Method used

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  • Synthesis method of 4,5,6,7-tetrahydrothieno[3,2-c]pyridine hydrochloride
  • Synthesis method of 4,5,6,7-tetrahydrothieno[3,2-c]pyridine hydrochloride
  • Synthesis method of 4,5,6,7-tetrahydrothieno[3,2-c]pyridine hydrochloride

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Embodiment 1

[0035] Put 32.7g (0.17mol) of p-toluenesulfonyl chloride and 40ml of dichloromethane into the reaction flask, cool down to -5°C, and add 20g (0.16mol) of 2-thiophenethanol. 28.4 g (0.28 mol) of triethylamine was slowly added dropwise, and the temperature of the reaction solution was kept at about 0°C. After the addition was completed, the reaction was incubated for 2 hours and then rose to room temperature. After the raw material 2-thiophene ethanol was consumed, suction filtered, and the solid was washed with a small amount of dichloromethane, and the filtrate was washed with 50 ml of saturated sodium bicarbonate, and dried over anhydrous sodium sulfate. Filtrate, concentrate the filtrate, freeze to precipitate a light brown solid, filter, and wash with a small amount of petroleum ether until white, which is 42.5 g of p-toluenesulfonate-2-thiopheneethyl ester, with a yield of 96.5% (HPLC purity 99%).

[0036] Put 5.64g (0.02mol) of 2-thiopheneethyl p-toluenesulfonate, 30ml o...

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Abstract

The invention relates to a synthesis method of 4,5,6,7-tetrahydrothieno[3,2-c]pyridine hydrochloride. The method comprises the following steps: synthesizing 2-(2-thienyl)ethyl p-toluenesulfonate from 2-thiopheneethanol and paratoluensulfonyl chloride, further reacting the 2-(2-thienyl)ethyl p-toluenesulfonate with formamide to synthesize N-2-thienylethylformamide, carrying out cyclization on the N-2-thienylethylformamide under the action of trifluoroacetic acid to produce 6,7-dihydrothieno[3,2-c]pyridine, reducing the 6,7-dihydrothieno[3,2-c]pyridine with sodium borohydride, and carrying out salification to obtain the 4,5,6,7-tetrahydrothieno[3,2-c]pyridine hydrochloride. The invention provides a novel method for synthesizing the 4,5,6,7-tetrahydrothieno[3,2-c]pyridine hydrochloride. The method has the characteristics of low cost, low toxicity and simple technique, and has industrialized application prospects.

Description

technical field [0001] The present invention relates to a synthesis method of 4,5,6,7-tetrahydrothieno[3,2-c]pyridine hydrochloride, especially a synthesis method using 2-thiophenethanol and p-toluenesulfonyl chloride as raw materials. A method for four-step synthesis of 4,5,6,7-tetrahydrothieno[3,2-c]pyridine hydrochloride. [0002] technical background [0003] 4,5,6,7-Tetrahydrothieno[3,2-c]pyridine hydrochloride is a pharmaceutical intermediate, mainly used in the synthesis of platelet coagulation inhibitors such as ticlopydine, clopidogrel, prasugrel and other drugs. Its structural formula is as follows: [0004] [0005] 4,5,6,7-Tetrahydrothiophene[3,2-c]pyridine hydrochloride has many synthetic methods. [0006] Most documents use 2-thiopheneethylamine as raw material to obtain 4,5,6,7-tetrahydrothiophene[3,2-c]pyridine hydrochloride by two-step method, and its synthetic route is: [0007] [0008] In the first step, 2-thienyl ethylamine reacts with formaldeh...

Claims

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Application Information

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IPC IPC(8): C07D495/04
CPCC07D495/04
Inventor 邢俊德严曙明卢建军沈国兵方正权冯秀娥宫顺全苗茂谦朱国峰
Owner TAIYUAN UNIV OF TECH
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