Acetic Acid → N-isopropyl-3,3-diphenylpropan-1-amine

Participants

Reaction Steps

To a solution of 3,3-diphenylpropan-1-amine 1 (4.22 g, 20.0 mmol) in DCE (100 mL) at room temperature was added acetone (1.19 g, 20.5 mmol, 1.50 mL), acetic acid (1.21 g, 20.1 mmol, 1.15 mL), and NaBH(OAc)3 (5.98 g, 28.2 mmol). The reaction mixture was stirred at room temperature for 5 min, a significant amount of precipitate formed, THF (40 mL) was added, and stirring was continued at room temperature for 3 h. The reaction mixture was quenched with 5 M NaOH, partially concentrated, and diluted with EtOAc. The aqueous phase was extracted with EtOAc (2×) and the combined organic extracts were washed with brine (1×), dried over MgSO4, filtered, and concentrated. Purification by flash column chromatography on silica gel (eluted with 2% to 8% MeOH (2 M NH3) in DCM) gave N-isopropyl-3,3-diphenylpropan-1-amine 2 (4.60 g, 90.9% yield) as a colorless oil.

Provenance & Evidence