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Preparation method of aniracetam

A technology of aniracetam and a catalyst, applied in the field of medicinal chemistry, can solve the problems of environmental pollution, long reaction time, low yield and the like, and achieve the effects of reducing cost, high atom utilization rate and good economic benefit

Inactive Publication Date: 2018-03-27
WUXI JIMIN KEXIN SHANHE PHARMA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] Through repeated experiments, we found that the products prepared by the above method generally have problems such as low yield, long reaction time, and serious environmental pollution.

Method used

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  • Preparation method of aniracetam
  • Preparation method of aniracetam
  • Preparation method of aniracetam

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Add 150ml of toluene, p-methoxybenzoic acid (34g, 0.2mol), α-pyrrolidone (17g, 0.2mol), sodium hydroxide (4g, 10mmol) into a 250mL four-neck flask, reflux after addition, and then distill off methanol . Methanol was evaporated off completely, cooled to 15°C, and a solid precipitated out. Filter to obtain a solid filter cake. Dissolve with 95% ethanol, decolorize with activated carbon, filter while hot, crystallize after cooling, filter, and dry the filter cake under reduced pressure to obtain 29.3 g of finished aniracetam. (Yield 67%). IR(KCl)2999cm -1 (Ar),1728cm -1 (CO); 1 H-NMR (CDCl 3 , TMS) 7.92 (2H, d, J = 9.2Hz, Ar), 7.17 (2H, d, J = 8.4Hz, Ar), 4.01 (2H, m, CH 2 ),3.83(3H,s,CH 3 ),2.35(2H,m,CH 2 ),2.09(2H,m,CH 2 ); MS (EI) m / z 219.0895 (M + ) analysis value: 219.0896; elemental analysis C 6 h 5 NO 4 , Found: C, 65.75; H, 5.97; N, 6.38; O, 21.88%. Calculated: C, 65.74; H, 5.98; N, 6.39;

Embodiment 2

[0039] In a 250mL four-neck flask, add 150ml of toluene, p-methoxybenzoic acid (34g, 0.2mol), α-pyrrolidone (17g, 0.2mol), potassium hydroxide (5.6g, 10mmol), reflux after addition, and then evaporate Methanol. Methanol was evaporated off completely, cooled to 15°C, and a solid precipitated out. Filter to obtain a solid filter cake. Dissolve with 95% ethanol, decolorize with activated carbon, filter while hot, crystallize after cooling, filter, and dry the filter cake under reduced pressure to obtain 29.5 g of finished aniracetam. (Yield is 68%)

Embodiment 3

[0041] Add 150ml of toluene, p-methoxybenzoic acid (34g, 0.2mol), α-pyrrolidone (17g, 0.2mol), silicon dioxide (6g, 10mmol) into a 250mL four-neck flask, reflux after addition, and then distill off methanol . Methanol was evaporated off completely, cooled to 15°C, and a solid precipitated out. Filter to obtain a solid filter cake. Dissolve with 95% ethanol, decolorize with activated carbon, filter while hot, crystallize after cooling, filter, and dry the filter cake under reduced pressure to obtain 39.5 g of finished aniracetam. (yield is 91%)

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Abstract

The present invention relates to medicinal chemistry field, be specifically related to a kind of preparation method of aniracetam, and its synthetic route is as follows:

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a preparation method of aniracetam. Background technique [0002] Aniracetam (also known as Aniracetam) is a new generation of beta-lactam brain function improving drugs, chemically named 1-(4-methoxybenzoyl)-2-pyrrolidone. Compared with piracetam, it has the advantages of strong action, quick onset and low toxicity. Clinically, it is mainly used to treat the sequelae of cerebrovascular diseases, and recent studies have shown that it also has a good curative effect on Alzheimer's disease (Liu Zhaoping. Foreign Medicine-Synthetic Drugs, Biochemical Drugs, Preparations, 1989; 10(5): 2 / 9.), can increase the level of acetylcholine in the patient's brain, is conducive to the transmission of cholinergic nerves, improves learning and memory capabilities, and has quick results, low toxicity, and has broad market prospects. [0003] The synthetic route of this medicine is as follows,...

Claims

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Application Information

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IPC IPC(8): C07D207/263
CPCC07D207/263
Inventor 姜迎庆夏一铜闵江
Owner WUXI JIMIN KEXIN SHANHE PHARMA
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