Hydrazine → HCID 66673247, compound

Participants

Reaction Steps

Hydrazine (0.140 mL, 4.45 mmol) was added to a mixture of 4-nitrophenyl 4-[({6-[4-(methylsulfonyl)phenyl]-3-pyridinyl}oxy)methyl]-1-piperidinecarboxylate (456 mg, 0.89 mmol) in ethanol (30 mL) at ambient temperature. The mixture was stirred at ambient temperature overnight. The mixture was charged with additional ethanol (30 mL) and hydrazine (5 mL, 159 mmol), stirred at reflux until homogeneous (15 min), then at ambient temperature overnight. The mixture was concentrated to dryness, charged with 4:1 EtOH:CH2Cl2 and MP-Carbonate (8 g). The mixture was stirred at ambient temperature for 2 h, filtered, washed with 4:1 EtOH:CH2Cl2, and the filtrate was concentrated to give 352 mg (98%) of 4-[({6-[4-(methylsulfonyl)phenyl]-3-pyridinyl}oxy)methyl]-1-piperidinecarbohydrazide as an off-white solid. 1H NMR (400 MHz, DMSO-d6): δ 8.43 (d, 1H, J=2.9 Hz), 8.28 (d, 2H, J=8.6 Hz), 8.06 (d, 1H, J=8.9 Hz), 7.99 (d, 2H, J=8.6 Hz), 7.61 (bs, 1H), 7.54 (dd, 1H, Ja=8.8 Hz, Jb=3.0 Hz), 4.03-3.92 (m, 4H), 3.84 (d, 2H, J=3.2 Hz), 3.25 (s, 3H), 2.74-2.64 (m, 2H), 2.05-1.88 (m, 1H), 1.79-1.67 (m, 2H), 1.23-1.09 (m, 2H); LRMS (ESI), m/z 405 (M+H).

Provenance & Evidence