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Synthetic method of eletriptan intermediate 4-nitrophenyl-2-(4-benzenesulfonyl hydrazide)ethane

A technology of eletriptan and benzenesulfonyl hydrazide, which is applied in the field of preparation of eletriptan intermediate 4-nitrophenyl-2-ethane, can solve the difficult problem of intermediate N-substituted aldehyde compounds acquisition, high cost of raw materials, high production cost, etc.

Inactive Publication Date: 2018-01-26
UNIV OF JINAN
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Problems solved by technology

[0007] There are some shortcomings in the above two preparation methods. In the first preparation method, a large amount of reductive debromination by-products will be produced by using a strong reducing agent lithium aluminum hydride. In addition, the intermediate N-substituted aldehydes are difficult to obtain, making the preparation higher cost
The second synthesis process uses expensive benzenesulfonyl ethylene, resulting in high raw material costs

Method used

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  • Synthetic method of eletriptan intermediate 4-nitrophenyl-2-(4-benzenesulfonyl hydrazide)ethane
  • Synthetic method of eletriptan intermediate 4-nitrophenyl-2-(4-benzenesulfonyl hydrazide)ethane
  • Synthetic method of eletriptan intermediate 4-nitrophenyl-2-(4-benzenesulfonyl hydrazide)ethane

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Embodiment Construction

[0014] 1 embodiment one: add benzenesulfonyl hydrazide 0.086g (0.50mmol) in the glass sealing tube of 10mL, p-nitrostyrene 0.298g (2.00mmol), then add dropwise 1mL water, 98% concentrated sulfuric acid 0.0029g (0.03 mmol), the reaction was carried out under magnetic stirring at 80 °C for 5 h. Stop heating, cool naturally, extract with ethyl acetate, rotary evaporate, and then use a silica gel column to separate, the chromatographic liquid is a mixed solvent of n-hexane: ethyl acetate (v / v=30:1), and use n-hexane for recrystallization: A mixed solvent of ethyl acetate (v / v=10:1) was used to obtain 0.132 g of 4-nitrophenyl-2-(4-benzenesulfonylhydrazide)ethane with a yield of 90.7% and a purity of 95.6%.

[0015] 2 Example 2: Add 0.086g (0.50mmol) of benzenesulfonylhydrazide and 0.298g (2.00mmol) of p-nitrostyrene to a 10mL glass sealed tube, then add dropwise 1mL of water, 0.0029g (0.03mmol) of concentrated hydrochloric acid , and reacted with magnetic stirring for 5 h at 80 °C...

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Abstract

The invention discloses a synthetic method of eletriptan intermediate 4-nitrophenyl-2-(4-benzenesulfonyl hydrazide)ethane. According to the synthetic method, 4-nitrostyrene and benzenesulfonyl hydrazide are taken as raw materials, distilled water is taken as a solvent, heating reaction is carried out under acidic conditions, and 4-nitrophenyl-2-(4-benzenesulfonyl hydrazide)ethane is obtained via one-step reaction. The synthetic method is capable of obtaining eletriptan important intermediate 4-nitrophenyl-2-(4-benzenesulfonyl hydrazide)ethane, yield is higher than 90%, purity is higher than 95%, the raw materials are cheap and easily available, operation is simple, side products are few, and the synthetic method is convenient for industrialized production.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a preparation method of eletriptan intermediate 4-nitrophenyl-2-(4-benzenesulfonylhydrazide)ethane. Background technique [0002] Eletriptan, the chemical name is (R)-3-[(1-methyl-2-pyrrolidinyl)methyl]-5-[2-(phenylsulfonyl)ethyl]-1H-indole , is suitable for the acute treatment of migraine with or without aura in adults, and has a good market application prospect. Wherein 4-nitrophenyl-2-(4-benzenesulfonyl hydrazide) ethane is an important intermediate for the preparation of eletriptan, research on 4-nitrophenyl-2-(4-benzenesulfonyl hydrazide) The synthesis method of ethane is of great significance to the research of eletriptan. [0003] Christopher P. et al. (Organic Process Research & Development, 2011, 15:98-103. ) reported a p-benzenesulfonyl-ethyl-phenylhydrazine and 3-(N-methyl-pyrrol-2-yl)- The method for synthesizing eletriptan by reaction of 1-propanal, it...

Claims

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Application Information

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IPC IPC(8): C07C303/40C07C303/44C07C311/49
Inventor 高令峰谷海洋郑庚修姚甜慧李薇崔召新
Owner UNIV OF JINAN
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