3,5-bis(arylidene)-N-benzenesulfonyl-4-piperidinone compounds and preparation method thereof
A technology of diaryl methylene and acetamidobenzenesulfonyl, which is applied in the field of anti-tumor and anti-inflammatory drugs and their preparation, can solve the problems of less research on benzenesulfonylation modification, and achieve favorable promotion and mild reaction conditions , the effect of high synthesis yield
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Embodiment 1
[0032] Synthesis of 3,5-bis(2-fluorobenzylidene)-N-(4-fluorobenzenesulfonyl)-4-piperidone (BAP-1)
[0033] Mix 0.01mol of 4-piperidone hydrochloride and 0.02mol of 2-fluorobenzaldehyde in a solution of 15mL of methanol and water, add 2-3mL of 20% sodium hydroxide solution dropwise at room temperature, and stir at 50°C for 6 hours , The end point of the reaction was determined by thin layer chromatography (TLC). After the reaction, the precipitate was suction filtered, and the resulting precipitate was washed with 70% aqueous methanol to obtain a yellow solid, namely the intermediate BAP-H (1). Then, the intermediate BAP-H (1) and 4-fluorobenzenesulfonyl chloride were dissolved in 10 mL Add 3-5 drops of pyridine to dichloromethane, stir overnight at room temperature, and determine the reaction end point by thin layer chromatography (TLC). The reaction solution was washed twice with 2mol / L=10:10:1) hydrochloric acid solution, and the reaction solution was concentrated under red...
Embodiment 2
[0036] Synthesis of 3,5-bis(3-nitrobenzylidene)-N-(4-fluorobenzenesulfonyl)-4-piperidone (BAP-2)
[0037] Mix 0.01mol of 4-piperidone hydrochloride and 0.02mol of 3-nitrobenzaldehyde in a solution of 15mL of methanol and water, add 2-3mL of 20% sodium hydroxide solution dropwise at room temperature, and stir at 40°C The reaction was carried out for 6 hours, and the end point of the reaction was determined by thin layer chromatography (TLC). After the reaction was completed, the precipitate was suction-filtered, and the resulting precipitate was washed with 70% aqueous methanol to obtain a yellow solid, the intermediate BAP-H (2). Then, the intermediate BAP-H (2) and 4-fluorobenzenesulfonyl chloride were dissolved in 10 mL Add 3-5 drops of pyridine to dichloromethane, stir overnight at room temperature, and determine the reaction end point by thin layer chromatography (TLC). The reaction solution was washed twice with 2mol / L hydrochloric acid solution, concentrated under reduc...
Embodiment 3
[0040] Synthesis of 3,5-bis(4-cyanobenzylidene)-N-(4-fluorobenzenesulfonyl)-4-piperidinone (BAP-3)
[0041] 0.01mol of 4-piperidone hydrochloride and 0.02mol of 4-cyanobenzaldehyde were mixed in 10mL of acetic acid, and dry hydrogen chloride gas was continuously introduced for 45min, stirred and reacted at 25°C for 8 hours, and passed thin layer chromatography ( TLC) to determine the end point of the reaction. After the reaction, the precipitate was suction filtered, the precipitate was dissolved in water and the pH value was adjusted to neutral with sodium hydroxide solution, and the resulting precipitate was washed with 70% methanol aqueous solution to obtain a yellow solid, which was the intermediate BAP-H (3). Then, the intermediate BAP-H(3) and 4-fluorobenzenesulfonyl chloride were dissolved in 10 mL of dichloromethane, 3-5 drops of pyridine were added, stirred at room temperature overnight, and the end point of the reaction was determined by thin layer chromatography (TL...
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