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Preparation method of gliclazide in green synthesis technology

A green synthesis and process technology, applied in the direction of organic chemistry, can solve the problems of difficult separation and purification of double salts, high environmental treatment costs, etc., and achieve the effects of improving reaction yield, facilitating industrial production, and mild reaction conditions

Active Publication Date: 2017-06-13
SHANDONG KEYUAN PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] This route is via KBH 4 / AlCl 3 After the reduction, a large amount of aluminum sludge and double salt will also be produced, and the separation and purification of the double salt is also difficult, resulting in high environmental treatment costs and the need to use the highly toxic substance hydrazine hydrate

Method used

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  • Preparation method of gliclazide in green synthesis technology
  • Preparation method of gliclazide in green synthesis technology
  • Preparation method of gliclazide in green synthesis technology

Examples

Experimental program
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Effect test

Embodiment 1

[0030] (1) Preparation of N-amino-3-azabicyclo[3,3,0]octane

[0031] Add 154g (1.0mol) of N-amino-1,2-cyclopentanedicarboximide, 700g of acetic acid, and copper-chromium catalyst (Cr-Cu atomic ratio 0.14) into a 2L high-pressure reactor with a stirring and heating device 4.6g, after stirring evenly, replace the air in the reactor with nitrogen, then replace the nitrogen in the reactor with hydrogen, and finally pressurize it to 1.5MPa with hydrogen, heat the reactor to 60°C, and react for 4 hours. After the reaction, Cool to room temperature, filter to remove the catalyst, concentrate the filtrate under negative pressure to remove the solvent acetic acid, add the residue to tetrahydrofuran, and use triethylamine to adjust the pH value of the solution to 6.5, filter, and distill the solvent from the filtrate to obtain a light yellow liquid N-amino-3-nitrogen Heterobicyclo[3,3,0]octane 114.28 (0.906mol) g, the yield was 90.6%, the crude product was directly used in the next reac...

Embodiment 2

[0037] (1) Preparation of N-amino-3-azabicyclo[3,3,0]octane

[0038]Add 154g (1.0mol) of N-amino-1,2-cyclopentanedicarboximide, 700g of acetic acid, and copper-chromium catalyst (Cr-Cu atomic ratio 0.2) into a 2L high-pressure reactor with a stirring and heating device 4.6g, after stirring evenly, replace the air in the reactor with nitrogen, then replace the nitrogen in the reactor with hydrogen, and finally pressurize it to 2MPa with hydrogen, raise the temperature of the reactor to 80°C, and react for 4 hours. After the reaction, cool To room temperature, filter to remove the catalyst, concentrate the filtrate under negative pressure to remove the solvent acetic acid, add tetrahydrofuran to the residue, and adjust the pH of the solution to 6.8 with triethylamine, filter, and distill the solvent from the filtrate to obtain a pale yellow liquid N-amino-3-azabicyclo [3,3,0]octane 115.3g (0.92mol), the yield was 91.37%, the crude product was directly used in the next reaction w...

Embodiment 3

[0044] (1) Preparation of N-amino-3-azabicyclo[3,3,0]octane

[0045] Add 154g of N-amino-1,2-cyclopentanedicarboximide, 700g of acetic acid, and 4.6g of copper-chromium catalyst (Cr-Cu atomic ratio 0.26) into a 2L high-pressure reactor with a stirring and heating device, and stir After uniformity, replace the air in the reactor with nitrogen, then replace the nitrogen in the reactor with hydrogen, and finally pressurize it to 2.5 MPa with hydrogen, heat the reactor to 90°C, and react for 4 hours. After the reaction, cool to room temperature. The catalyst was removed by filtration, the filtrate was concentrated under negative pressure to remove the solvent acetic acid, the residue was added to tetrahydrofuran, and the pH of the solution was adjusted to 7 with triethylamine, filtered, and the solvent was distilled from the filtrate to obtain a pale yellow liquid N-amino-3-azabicyclo[3, 3,0] Octane 118.6g, the yield was 93.97%, the crude product was directly used in the next reac...

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Abstract

The present invention provides a gliclazide green synthesis process which is simple in process, safe and environmentally-friendly, and convenient to actually operate, N-amino-1, 2-cyclohexane dicarboximide is used as a raw material, the gliclazide green synthesis process mainly includes the following steps: N-amino-3-azabicyalo[3, 3, 0] octane is prepared by high pressure hydrogenation of the N-amino-1, 2-cyclohexane dicarboximide, the N-amino-3-azabicyalo[3, 3, 0] octane is reacted with phosgene in high pressure conditions to prepare N-(hexahydrocyclopentadiene[c] pyrrole-2(1H)-yl)-amino chloride, and finally gliclazide prepared by condensation reaction of the N-(hexahydrocyclopentadiene[c] pyrrole-2(1H)-yl)-amino chloride and para toluene sulfonamide.

Description

technical field [0001] The invention relates to the field of preparation methods of sulfonylurea hypoglycemic drugs, in particular to a preparation method of gliclazide. Background technique [0002] Gliclazide, English name: Gliclazide, molecular formula: C 15 h 21 N 3 o 3 S, chemical name 1-[hexahydrocyclopenta(C)pyrrol-2(1H)-yl]-3-(4-methylphenyl)sulfonylurea. Gliclazide is a second-generation sulfonylurea oral hypoglycemic drug, which has dual functions of lowering blood sugar and improving blood coagulation function. It can not only improve the metabolism of diabetic patients, but also improve or delay the occurrence of diabetic vascular complications. Gliclazide was developed by the French SERVEIR company and launched in France in 1972. It has been widely used in clinical practice at home and abroad, and has become one of the most commonly used drugs for the treatment of type 2 diabetes. It is also the first-line oral hypoglycemic drug in my country. Its chemical ...

Claims

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Application Information

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IPC IPC(8): C07D209/52
CPCC07D209/52
Inventor 伦立军任小亮王广洪陈玉玺闫希路刘璇
Owner SHANDONG KEYUAN PHARMA
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