1-Methylpiperazine → 1-[3-(3-Fluoro-piperidin-1-yl)-4-nitro-phenyl]4-methyl-piperazine

Participants

Reaction Conditions

Reaction Steps

A solution of 1-(5-chloro-2-nitro-phenyl)-3-fluoro-piperidine (as prepared in the previous step, 0.44 g, 1.7 mmol) in N-methylpiperazine (2 mL) was heated to 80° C. for 18.5 h. The reaction was cooled to room temperature, diluted with CH2Cl2 and washed with water. The aqueous layer was extracted with CH2Cl2. The combined organic layers were dried over MgSO4 and concentrated in vacuo to afford the title compound (0.50 g, 93%) as a yellow solid. 1H-NMR (CDCl3; 400 MHz): δ 8.00 (d, 1H, J=9.2 Hz), 6.44 (dd, 1H, J=9.2 Hz, J=2.8 Hz), 6.34 (d, 1H, J=2.8 Hz), 4.91-4.71 (m, 1H), 3.54-3.44 (m, 1H), 3.41-3.36 (m, 4H), 3.18-3.10 (m, 1H), 3.02-2.94 (m, 1H), 2.87-2.80 (m, 1H), 2.5-2.52 (m, 4H), 2.35 (s, 3H), 1.82-1.66 (m, 4H). LC-MS (ESI, m/z): Calcd. for C16H23FN4O2 323.2 (M+H), found 323.2.

Provenance & Evidence