2-Pyridineethanamine → 3,3-bis(4-fluorophenyl)-N-(2-(pyridin-2-yl)ethyl)propan-1-amine

Participants

Reaction Steps

To a solution of 3,3-bis(4-fluorophenyl)propanal (0.967 g, 3.93 mmol) in DCE (15 mL) at room temperature was added 2-(pyridin-2-yl)ethanamine (1.73 g, 14.2 mmol) and NaBH(OAc)3 (1.08 g, 5.10 mmol). The reaction mixture was stirred at room temperature for 17 h, diluted with EtOAc, washed with 5 M NaOH (1×), brine (1×), dried over MgSO4, filtered, and concentrated. Purification by flash column chromatography on silica gel (eluted with 2% to 8% MeOH (2M NH3) in DCM) followed by purification by flash column chromatography on silica gel (eluted with 50% to 100% EtOAc (10% 2M NH3 in MeOH) in hexanes) gave 3,3-bis(4-fluorophenyl)-N-(2-(pyridin-2-yl)ethyl)propan-1-amine.

Provenance & Evidence