Benzaldehyde → HCID 10364246, compound

Participants

Reaction Steps

A solution of amine 50 (0.22 g, 0.68 mmol) and benzyaldehyde (0.07 mL, 0.08 mmol) in EtOH (3.0 mL) was heated at reflux overnight before it was allowed to cool to room temperature. Sodium borohydride (0.04 g, 0.80 mmol) was added and the reaction was stirred at room temperature for 1 hour. The mixture was mixed with 2N NaOH (3.0 mL), brine (2.0 mL), and extracted with 7:3 CH2Cl2/MeOH (3×5.0 mL). The combined organic layers were dried (K2CO3) and concentrated under reduced pressure. The residue was purified by flash chromatrography (SiO2, gradient elution, 3:1 hexanes/EtOAc to 7:3 CH2Cl2/MeOH) to yield the desired product (0.15 g, 62%) as a pale yellow solid.

Provenance & Evidence