Dichloromethane → Dichloromethane methanol ammonium hydroxide

Participants

Reaction Steps

To a solution of (9H-fluoren-9-yl)methyl 1-(6-fluoro-1-(4-fluorophenyl)-1H-benzo[d]imidazol-2-yl)ethylcarbamate (3.38 g, 6.82 mmol) in DCM (34.1 mL) was added piperidine (0.809 mL, 8.19 mmol) and the mixture was stirred at rt. After 4 days, the mixture was concentrated under reduced pressure to give a brown solid. The brown solid was purified by column chromatography on a 120 g of Redi-Sep column using 0 to 100% gradient of DCM:MeOH:NH4OH (89:9:1) in DCM over 27 min and then 100% isocratic of DCM:MeOH:NH4OH (89:9:1) for 5 min as eluent to give 1-(6-fluoro-1-(4-fluorophenyl)-1H-benzo[d]imidazol-2-yl)ethanamine over three steps as a pink syrupy solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.67 (3H, td, J=8.8, 5.0 Hz), 7.48 (2H, t, J=8.8 Hz), 7.09 (1H, ddd, J=9.8, 8.8, 2.5 Hz), 6.88 (1H, dd, J=9.0, 2.3 Hz), 3.93 (1H, q, J=6.8 Hz), 1.92 (2H, br. s.), 1.33 (3H, d, J=6.7 Hz); LC-MS (ESI) m/z 274.0 [M+H]+.

Provenance & Evidence