Potassium Carbonate → 6-(2-(4-p-tolylpiperidin-1-yl)ethyl)-2H-benzo[b][1,4]oxazin-3(4H)-one

Participants

Reaction Conditions

Reaction Steps

To a 20 mL screw cap vial was added 123 (100 mg, 0.472 mmol), 4-p-tolylpiperidine (83 mg, 0.472 mmol), K2CO3 (131 mg, 0.945 mmol) in DMF (2 mL). The reaction was stirred at 80° C. for 4 h. The reaction was filtered and the crude material was purified by prep HPLC-MS using a 25-95% MeCN in water gradient. The appropriate fractions were collected and concentrated in vacuo to give the title compound as a white solid: 1H NMR (DMSO-d6, 400 MHz): δ=10.79 (br. s., 1H), 9.27 (br. s., 1H), 7.14 (br. s., 4H), 6.94 (br. s., 1H), 6.80-6.87 (m, 1H), 6.78 (br. s., 1H), 4.56 (br. s., 2H), 3.65 (br. s., 2H), 3.27 (br. s., 2H), 3.08 (br. s., 2H), 2.94 (br. s., 2H), 2.78 (br. s., 1H), 2.28 (br. s., 3H), 2.00 (br. s., 2H), 1.82 ppm (br. s., 2H). ESI-MS: m/z 351.2 (M+H)+.

Provenance & Evidence