Preparation method and application of N-substituted-3,5-dibenzal piperidine-4-one
A bisbenzylidene piperidine, phenyl technology, applied in the field of new anti-leukemia K562 cell proliferation drug lead compounds, can solve the problem of chronic myeloid leukemia being difficult to cure, and achieve obvious novelty and creativity, easy production, and remarkable practicality sexual effect
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Embodiment 1
[0050] Example 1: Preparation of (Ia) N-(4-methylbenzyl)-3,5-bisbenzylidenepiperidin-4-one.
[0051] At room temperature, add 0.16mol methyl acrylate and 7mL methanol into a 100mL three-necked flask, stir, and slowly add a mixture of 0.04mol p-methylbenzylamine and 4mL methanol into the three-necked flask, so that the temperature of the reaction system does not exceed 50 ℃. After the dropwise addition, heat to reflux for 8 hours. After the reaction is over, recover methanol and unreacted methyl acrylate, and distill under reduced pressure to obtain light yellow oily liquid N, N-bis(β-methyl propionate) p-methyl Benzylamine (2a).
[0052] Add 15mL of anhydrous toluene and 0.122mol of sodium metal to a 250mL dry three-necked flask, stir and heat to reflux, add 0.2mL of anhydrous methanol, and then slowly add 0.04mol of N,N-bis(β-propionate methyl ester) to A mixture of methylbenzylamine (2a) and 20mL of anhydrous toluene. After the dropwise addition was completed, it was refl...
Embodiment 2
[0055] Example 2: Preparation of (Ib) N-(4-methylbenzyl)-3,5-bis(4-methylbenzylidene)piperidin-4-one.
[0056] N-p-methylbenzylpiperidin-4-one (4a) obtained by the preparation method of Example 1, take N-p-methylbenzylpiperidin-4-one (4a) 0.005mmol and 0.01mol p-methylbenzylpiperidin-4-one Base benzaldehyde was mixed in a 50mL dry round bottom bottle, 15mL of absolute ethanol was added, and 1mL of 10% NaOH was added during stirring, and solids precipitated after 40min. After the reaction, the solid was washed with ethanol, and recrystallized with ethyl acetate and petroleum ether to obtain N-(4-methylbenzyl)-3,5-bis(4-methylbenzylidene)piperidine-4 - Ketones (Ib).
[0057] Yield: 82%; yellow solid, mp 170-171℃; 1 H NMR (400MHz, CDCl 3 )δ2.28(s, 3H), 2.36(s, 6H), 3.66(s, 2H), 3.83(s, 4H), 7.04(d, J=7.8Hz, 2H), 7.13(d, J=7.9 Hz, 2H), 7.17(d, J=8.0Hz, 4H), 7.25(d, J=8.1Hz, 4H), 7.76(s, 2H); IR (KBr): 2916, 2745, 1670, 1613, 1578 , 1558, 1264, 1180, 1072, 813em -1 ;Anal.calc...
Embodiment 3
[0058] Example 3: Preparation of (Ic) N-(4-methylbenzyl)-3,5-bis(4-methoxybenzylidene)piperidin-4-one.
[0059] N-p-methylbenzylpiperidin-4-one (4a) obtained by the preparation method of Example 1, take N-p-methylbenzylpiperidin-4-one (4a) 0.005mmol and 0.01mol p-methylbenzylpiperidin-4-one Oxybenzaldehyde was mixed in a 50mL round bottom bottle, 15mL of absolute ethanol was added, 1mL of 10% NaOH was added with stirring, and stirred at room temperature for 30min, a yellow solid was precipitated, and the reaction progress was tracked by thin layer chromatography (TLC). After the reaction is over, wash the solid with ethanol, and recrystallize with ethyl acetate and petroleum ether to obtain N-(4-methylbenzyl)-3,5-bis(4-methoxybenzylidene)piperidine- 4-keto (Ic).
[0060] Yield: 87%; yellow solid, mp 172-174℃; 1 H NMR (400MHz, CDCl 3 )δ2.28(s, 3H), 3.66(s, 2H), 3.84(s, 4H), 3.91(s, 6H), 7.04(d, J=7.8Hz, 2H), 7.13(d, J=7.9 Hz, 2H), 7.25(d, J=8.3Hz, 4H), 7.42(d, J=8.4Hz, 4H),...
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