Triphenylphosphine → 1-(4-{4-[(1-cyclobutylpiperidin-4-yl)oxy]phenyl}tetrahydro-2H-pyran-4-yl)-N,N-dimethylmethanamine

Participants

Reaction Steps

4-(4-Dimethylaminomethyl-tetrahydro-pyran-4-yl)-phenol (0.75 g, 3.19 mmol), 1-cyclobutylpiperidin-4-ol (0.45 g, 2.90 mmol), PPh3 (0.84 g, 3.19 mmol), THF (10 ml) and DIAD (0.66 ml, 3.19 mmol) were reacted together similarly to general procedure C. The crude material was subjected to chromatography on silica gel eluting with dichloromethane:methanol:ammonia (98:2:0.2) to provide the title compound (114 mg, 11%) as an off-white solid. 1H NMR (400 MHz, CD3OD) δ 1.71-1.77 (m, 4H), 1.85-1.90 (m, 4H), 1.94 (s, 6H), 1.99-2.06 (m, 4H), 2.12-2.16 (m, 2H), 2.20-2.28 (m, 2H), 2.45 (s, 2H), 2.58-2.70 (m, 2H), 2.79 (m, 1H), 3.46-3.53 (m, 2H), 3.72-3.75 (m, 2H), 4.39 (m, 1H), 6.91 (d, 2H), 7.26 (d, 2H). HRMS ESI+ m/z 373.2846 [MH]+.

Provenance & Evidence