Preparation method of bisacodyl

A bisacodyl and pyridine technology, applied in the field of bisacodyl preparation, can solve the problems of complex operation, difficult to obtain raw materials, unsuitable for industrial production, etc., and achieve high reaction yield, saving raw materials, and easy operation

Inactive Publication Date: 2012-12-19
HEBEI KANGTAI PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The synthesis method is complex in operation, and the raw materials are not easy to obtain, so it is not suitable for industrial production

Method used

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  • Preparation method of bisacodyl
  • Preparation method of bisacodyl
  • Preparation method of bisacodyl

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Synthesis of 4',4"-dihydroxydiphenyl-(2-pyridine)-methane

[0030] In a 250ml three-neck flask, at 0-5°C, add 13ml (23.92g) of concentrated sulfuric acid, stir and add 24g of phenol, stir for 2 hours, at 5-15°C, add dropwise 8ml of 2-pyridinecarbaldehyde (9.008g), for 1 hour After the dropwise addition, stir and react at room temperature for 1 hour; cool in an ice bath, add 40ml of water at 0-10°C, stir for 10 minutes, adjust the pH value to 7 with 2mol / L sodium hydroxide solution, stir for 2 hours, and then add 25ml of ethyl acetate, stirred for 10 minutes, filtered to obtain 15g of white solid, detected by NMR as 4',4"-dihydroxydiphenyl-(2-pyridine)-methane, melting point 238-240°C, yield 68% The filtrate obtained by filtration was adjusted to pH 1 with sulfuric acid, stirred for 0.5 hours, the ethyl acetate layer was separated, and 90ml of ethyl acetate was added to extract the water layer three times, the organic phases were combined, concentrated, and dried over an...

Embodiment 2

[0036] Synthesis of 4',4"-dihydroxydiphenyl-(2-pyridine)-methane

[0037] In a 500ml three-necked flask, add 24ml of concentrated sulfuric acid at 0-5°C, stir and add 26g of phenol, stir for 2 hours, and add 16ml of 2-pyridinecarbaldehyde dropwise at 5-15°C, add dropwise in 1 hour, and stir at room temperature React for 1.5 hours; cool in an ice bath, add 100ml of water at 0-10°C, stir for 10 minutes, adjust the pH to 7 with 2mol / L sodium hydroxide solution, stir for 2 hours, and filter with suction to obtain 42g of a yellow solid. Then the yellow solid was recrystallized several times with ethanol to obtain 12 g of white solid, identified as 4',4"-dihydroxydiphenyl-(2-pyridine)-methane by NMR, melting point 238-240°C, 4',4 "-Dihydroxydiphenyl-(2-pyridine)-methane yield: 26%. The resulting mother liquor was spin-dried to obtain 30 g of a yellow solid, which was analyzed by HPLC to contain 4', 4"-dihydroxydiphenyl-(2-pyridine)-methane and 2', 4"-dihydroxydiphenyl The ratio of...

Embodiment 3

[0039] Synthesis of 4',4"-dihydroxydiphenyl-(2-pyridine)-methane and 2',4"-dihydroxydiphenyl-(2-pyridine)-methane

[0040] In a 250ml three-neck flask, add 13ml of concentrated sulfuric acid at 0-5°C, stir and add 24g of phenol, and after stirring for 2 hours, add 8ml of 2-pyridinecarbaldehyde dropwise at 0-5°C, add dropwise in 1 hour, and stir at room temperature React for 1 hour; add 40ml of water at 0-5°C, stir for 10 minutes, adjust the pH to 7 with 2mol / L sodium hydroxide solution, and stir for 2 hours; filter with suction to obtain 20g of a yellow solid. The yellow solid was then recrystallized with methanol and water to obtain 10 g of a white solid identified by NMR as 4',4"-dihydroxydiphenyl-(2-pyridine)-methane, melting point 238-240°C, 4',4 "-Dihydroxydiphenyl-(2-pyridine)-methane yield: 43%. After adding methanol and water for recrystallization, the resulting mother liquor was spin-dried, and recrystallized with ethanol to obtain 1.0 g of a white solid, which was i...

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Abstract

The invention relates to a preparation method of bisacodyl, which comprises the following steps of: by adopting sulphuric acid as a catalyst, carrying out condensation reaction on 2-pyridylaldehyde and phenol at 0-15 DEG C; regulating pH to be 7.0 by using 2mol / L sodium hydroxide; stirring for 2 hours; then, adding ethyl acetate and filtering to obtain 4',4''-dihydroxydiphenyl-(2- pyridine)-methane; adding the 4',4''-dihydroxydiphenyl-(2-pyridine)-methane, methylene dichloride and 2mol / L sodium hydroxide; adding 4-dimethylamino pyridine (DMAP) as a catalyst; then, adding acetic anhydride for reaction for 0.5 hour at room temperature; concentrating and drying to obtain crude products of bisacodyl; and recrystallizing the crude products of the bisacodyl with ethanol to obtain high-purity bisacodyl. The method has the advantages that the process is simple and can be easily operated, the product yield is high and can reach 61 percent after the purification, the purity of the bisacodyl is high with the content is 99 percent, the phenol can be recovered so taht the resource waste is avoided and the environment production is alleviated, and the production cost is low.

Description

technical field [0001] The invention relates to a preparation method of bisacodyl, in particular to an improved preparation method of bisacodyl. Background technique [0002] Bisacodyl, Bisacodyl, the chemical name is 4,4'-(2-pyridine methylene)-diphenol diacetate, is an excellent laxative widely used at home and abroad, it can directly contact with the intestinal mucosa, Stimulate its sensory nerve endings, causing increased intestinal reflex peristalsis, resulting in defecation. For the research on the synthesis method of bisacodyl, there are related reports in patents and literature. The synthetic routes in these reported synthetic methods are as follows: [0003] [0004] [0005] There are roughly two different processing methods for the above synthetic route. The first method is to generate 4', 4"-dihydroxydiphenyl-(2-pyridine)-methane and the ortho isomer 2' after the first step reaction , a mixture of 4"-dihydroxydiphenyl-(2-pyridine)-methane, the mixture wa...

Claims

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Application Information

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Patent Type & AuthorityPatents(China)
IPC IPC(8): C07D213/30
Inventor张军辉李洪玉李金岭姜申德
OwnerHEBEI KANGTAI PHARMA