p-Toluenesulfonic acid monohydrate → HCID 59424354, compound

Participants

Reaction Steps

3-(1-Benzylpiperidin-4-yl)-4-hydroxy-3,4-dihydroquinolin-2(1H)-one (1.6 mmol, 550 mg) was suspended in benzene (10 mL). p-Toluenesulfonic acid monohydrate (1.9 mmol, 370 mg) was added to the mixture. Reaction was heated to reflux and held for 1 hour. Reaction mixture was concentrated in vacuo. Residue was dissolved in 10% ethanol-dichloromethane (50 mL). Mixture was washed 2× with aqueous sodium bicarbonate. Organic layer was dried (magnesium sulfate), filtered and concentrated in vacuo. Residue was triturated with diethyl ether. Solids were filtered off, washed with diethyl ether, then dried in vacuo. Title compound was obtained as off-white solid in 63% yield. 1H NMR (300 MHz, DMSO-d6): δ=11.72 (s, 1H), 7.72 (s, 1H), 7.62 (d, J=6.95, 1H), 7.47-7.38 (m, 1H), 7.35-7.30 (m, 4H), 7.29-7.20 (m, 2H), 7.14 (t, J=7.50, 1H), 3.49 (s, 3H), 2.92 (d, J=11.34, 2H), 2.83-2.69 (m, 1H), 2.04 (t, J=10.61, 2H), 1.78 (d, J=12.08, 2H), 1.71-1.47 (m, 2H). MS m/e (M+H)+=319.3.

Provenance & Evidence