Dichloromethane → N-(5-bromo-2-nitrophenyl)-1-(tetrahydro-2H-pyran-4-yl)-4-piperidinamine

Participants

Reaction Steps

To a mixture of 4-bromo-2-fluoro-1-nitrobenzene (1.05 g, 0.0048 mol) and 1-(tetrahydro-2H-pyran-4-yl)-4-piperidinamine (0.883 g, 0.0048 mol) D9 in dimethylformamide (10 mL) was added diisopropylethylamine (1.175 mL, 0.0068 mol). The resulting mixture was sealed in a 20 mL Biotage Process Vial and irradiated at 200° C. for 1 min in the Smith Synthesizer. After irradiation, dichloromethane (15 mL) was added to the reaction solution. The resulted solution was washed with H2O (2×10 mL). The combined aqueous layers were extracted with dichloromethane (2×10 mL). The organic layers were combined, dried with Na2SO4, and concentrated in vacuo to yield the title compound (1.8 g) which was used in next step directly without purification. MS (ESI): 384 [M+]; 1H NMR (400 MHz, CDCl3): δ 1.68 (6H, m), 2.09 (2H, d), 2.49 (3H, m), 2.89 (2H, d), 3.39 (2H, t), 3.51 (1H, m), 4.04 (2H, dd), 6.72 (1H, dd), 7.01 (1H, d), 8.03 (1H, d), 8.14 (1H, d).

Provenance & Evidence