A kind of paeonol oxime ether compound, its preparation method and medical application
An ether compound, paeonol oxime technology, applied in the field of medicinal chemistry and pharmacotherapeutics, can solve the problem of easy sublimation of paeonol
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Embodiment 1
[0122] Preparation of Ethyl Paeonol Ether (1)
[0123]Weigh 2.0g (12mmol) of paeonol and 3.0g (75mmol) of sodium hydroxide in a 100mL round bottom flask, add DMF to dissolve, add bromoethane (1.8mL, 24mmol) dropwise under stirring, and react at 45°C , and TLC monitored the progress of the reaction. After the reaction is complete, add 100 mL of dichloromethane to dilute the reaction solution, wash with saturated brine (50 mL×3), concentrate the organic phase, and separate by column chromatography (the mobile phase is ethyl acetate:petroleum ether (v:v)=1:4) 2.3 g of white solid was obtained, with a yield of 98.2%. m.p.69.5~70.2℃.
[0124] Preparation of ethyl paeonol oxime (2)
[0125] Weigh 2.0g (10.3mmol) of ethylpaeonol ether into a 50mL round bottom flask, add 30mL of absolute ethanol to dissolve, add hydroxylamine hydrochloride (2.1g, 30.9mmol) and pyridine (4mL, 103.0mmol) in turn, 50°C The reaction was stirred, and the progress of the reaction was monitored by TLC. ...
Embodiment 2
[0131] With reference to the method of Example 1, ethyl paeonol oxime was prepared.
[0132] Preparation of ethyl paeonol oxime bromopropyl ether (3)
[0133] Weigh 2.0g (9.5mmol) of ethyl paeonol oxime into a 50mL round bottom flask, add 10ml of DMF to dissolve. Under ice-bath conditions, NaH (0.7g, 28.5mmol) was added, and after stirring for five minutes, 1,3-dibromopropane (28.5mmol) was added, and the reaction was stirred in an ice-bath, and the reaction progress was monitored by TLC. After 0.5 h of reaction, the reaction solution was poured into 100 mL of ice water, extracted with dichloromethane (50 mL×3), the organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, concentrated, and subjected to column chromatography (ethyl acetate:petroleum ether ( v:v)=1:10) to obtain 2.6 g of colorless oily liquid with a yield of 83.5%.
[0134] Ethylpaeonol oxime 3-(1-morpholinyl)propyl ether (I 9 ) preparation
[0135] Weigh 954 mg (2.9 mmol) of ethox...
Embodiment 3
[0137] With reference to the method of Example 1, ethyl paeonol oxime was prepared.
[0138] Preparation of ethyl paeonol oxime bromobutyl ether (3)
[0139] Weigh 2.0g (9.5mmol) of ethyl paeonol oxime into a 50mL round bottom flask, add 10ml of DMF to dissolve. Under ice-bath conditions, NaH (0.7g, 28.5mmol) was added, and after stirring for five minutes, 1,4-dibromobutane (3.4ml, 28.5mmol) was added, and the reaction was stirred in an ice-bath, and the reaction progress was monitored by TLC. After 0.5 h of reaction, the reaction solution was poured into 100 mL of ice water, extracted with dichloromethane (50 mL×3), the organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, concentrated, and subjected to column chromatography (ethyl acetate:petroleum ether ( v:v)=1:10) to obtain 2.6 g of colorless oily liquid with a yield of 81.2%.
[0140] Ethylpaeonol oxime 4-[(4-ethyl)-1-piperazinyl]butyl ether (I 18 ) preparation
[0141] Weigh 1.0 g (2.9 ...
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