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Method for preparing derivatives of cis-oximes and oxime ethers

A technology of derivatives and oxime ethers, applied in the field of medicinal chemistry, can solve the problems of low yield, unfavorable industrial production, complicated operation, etc., and achieve the effect of good product quality, low cost and simple operation

Inactive Publication Date: 2011-01-12
TIANJIN INSTITUTE OF PHARMA RESEARCH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The existing methods are relatively complicated to operate, and the yield is not high, which is unfavorable for industrialized production

Method used

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  • Method for preparing derivatives of cis-oximes and oxime ethers
  • Method for preparing derivatives of cis-oximes and oxime ethers

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Example 1 2'-Fluoro-4-hydroxychalcone-Z-oxime

[0025] In a 1L flask equipped with stirring, thermometer, and reflux condenser, add 2,-fluoro-4-hydroxychalcone (50.0g, 0.2mol), hydroxylamine hydrochloride (69.5g, 1.0mol), sodium acetate (65.6g , 0.8mol), 600mL absolute ethanol, pH4~6, react at 40℃ for 6h. The solvent was distilled off under reduced pressure to obtain a yellow-brown viscous substance, which was added with 1 L of water and 1 L of dichloromethane, separated into layers, and the organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain a pale yellow solid. 250ml of diethyl ether was crystallized to obtain 40.5g of white crystals with a melting point of 196-200°C and a yield of 75%. HPLC determination (0.02mol·L -1 Dipotassium hydrogen phosphate: acetonitrile: methanol: = 2:1:1, Z-type content > 85%)

[0026] 1 HNMR (400MHz, DMS O), δ (ppm) 6.30 (1H, d, H-C=) 6.70 (2H, d, H 3，5 )6.95(1H, d, H...

Embodiment 2

[0027] Example 2 2'-Fluoro-4-hydroxychalcone-Z-oxime

[0028] In a 1L flask equipped with stirring, thermometer and reflux condenser, add 2'-fluoro-4-hydroxychalcone (50.0g, 0.2mol), hydroxylamine hydrochloride (69.5g, 1.0mol), anhydrous potassium carbonate ( 110.6g, 0.8mol), 600mL absolute ethanol, pH4~6, reflux for 4h. The insoluble matter was filtered off, and the solvent was distilled off under reduced pressure to obtain a yellow-brown viscous substance. Add 1L of water and 1L of dichloromethane, separate layers, and dry the organic layer over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain a pale yellow solid. 250ml of diethyl ether was crystallized to obtain 45.2g of white crystals with a melting point of 196-200°C and a yield of 83.7%. HPLC determination (0.02mol L-1 dipotassium hydrogen phosphate: acetonitrile: methanol: = 2: 1: 1, Z-type content > 90%)

[0029] 1 HNMR (400MHz, DMSO), δ (ppm) 6.30 (1H, d, H-C=) 6.80 (2H, ...

Embodiment 3

[0030] Example 3 2'-Fluoro-4-hydroxychalcone-Z-oxime

[0031]In a 1L flask equipped with stirring, a thermometer, and a reflux condenser, add 2'-fluoro-4-hydroxychalcone (50.0g, 0.2mol), hydroxylamine hydrochloride (69.5g, 1.0mol), 600mL absolute ethanol, 1% sodium hydroxide ethanol solution to adjust the pH to 4-6, magnesium oxide 5g, reflux reaction for 8h. The solvent was distilled off under reduced pressure to obtain a yellow-brown viscous substance, which was added with 1 L of water and 1 L of dichloromethane, separated into layers, and the organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain a pale yellow solid. 250ml of diethyl ether was crystallized to obtain 38.9g of white crystals with a melting point of 196-200°C and a yield of 72%. HPLC determination (0.02mol·L -1 Dipotassium hydrogen phosphate: acetonitrile: methanol: = 2:1:1, Z-type content > 80%)

[0032] 1 HNMR (400MHz, DMSO), δ (ppm) 6.30 ...

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Abstract

The invention provides a method for preparing derivatives of cis-oximes and oxime ethers. The method comprises the following steps of: dissolving chalcone, chalcone derivatives and hydroxylamine or alcoxyl amine salt in a solvent, adjusting a pH value of the solution to a proper value, and adding a catalyst to obtain the cis-oxime or oxime ether compounds. The method has the advantages of obtaining the cis products by one-step reaction, along with easy and convenient operation and suitability for mass production. The invention also provides the oximes and oxime ethers prepared by the method, and the oximes and oxime ethers have the characteristics of high yield and high purity.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a method for preparing cis-chalcone oxime and oxime ether derivatives. Background technique [0002] 5-HT (5-hydroxytryptamine), as an endogenous active substance of the human body, is closely related to many physiological and pathological activities of the human body. As a neurotransmitter, 5-HT can participate in the regulation of various physiological functions and pathological states in the brain. Such as the regulation of sleep, food intake, body temperature, and mental and emotional diseases (Foreign Medical Psychiatry, 1998, 25: 95-97). Current research shows that 5-HT2 A (i.e. 5-HT2 A Receptor) receptor antagonists can be used for the treatment of mental diseases such as depression, anxiety and insomnia. Eplivanserin is a specific 5-HT2 A Receptor antagonists are mainly used clinically to treat insomnia symptoms such as short sleep duration and frequent awakenings a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C249/08C07C251/48C07C251/58
Inventor 李玲罗振福张越赵世明
Owner TIANJIN INSTITUTE OF PHARMA RESEARCH
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