Propanal → HCID 10729576, compound

Participants

Reaction Steps

To a solution of 3,3-diphenylpropan-1-amine 1 (4.22 g, 20.0 mmol) in MeOH (100 mL) at room temperature was added propionaldehyde (1.16 g, 20.0 mmol) (1.45 mL). The reaction mixture was stirred at room temperature for 3 h and sodium borohydride (1.20 g, 31.7 mmol) was added. The reaction mixture was stirred at room temperature for 2 h, quenched with 5 M NaOH, partially concentrated, and diluted with EtOAc. The aqueous phase was extracted with EtOAc (2×) and 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 3,3-diphenyl-N-propylpropan-1-amine 7 as a pale yellow oil.

Provenance & Evidence