Dimethyl Sulfoxide → 1'-[3-(Methyloxy)-4-nitrophenyl]-1,4'-bipiperidine

Participants

Reaction Steps

To 5-fluoro-2-nitrophenyl methyl ether (26.0 g, 152 mmol), 1,4′-bipiperidine (25.5 g, 152 mmol) and K2CO3 (22.9 g, 166 mmol) was added DMSO (260 mL). The mixture was stirred at room temperature for 3 days. The mixture was poured into H2O (1000 mL) and the H2O washed with EtOAc (2×500 mL). The EtOAc washes were combined and washed with H2O (2×500 mL). The ether layer was dried (MgSO4), filtered, and rotovaped down to give the title compound (47.9 g, 150 mmol, 99%) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ 7.98 (d, J=9.5 Hz, 1H), 6.40 (dd, J=9.5 and 2.6 Hz, 1H), 6.29 (d, J=2.6 Hz, 1H), 3.99-3.93 (m, 2H), 3.93 (s, 3H), 2.98-2.89 (m, 2H), 2.58-2.48 (m, 5H), 1.99-1.90 (m, 2H), 1.70-1.55 (m, 8H), 1.48-1.40 (m, 2H).

Provenance & Evidence