4-Methoxybenzaldehyde → Hept-6-enyl-(4-methoxy-benzyl)-amine

Participants

Reaction Steps

A solution of hept-6-enylamine (2.0 g, 13.4 mmol) and anisaldehyde (1.79 mL, 14.7 mmol) in EtOH (50 mL) was stirred at room temperature for 1 h. Then, NaBH4 (556 mg, 14.7 mmol) was added at 0° C. under nitrogen. The resulting solution was allowed to warm up to room temperature for 4 h. Then, the reaction mixture was partitioned between ice-cold water and CH2Cl2, washed with brine, dried (Na2SO4) and evaporated. The residue was purified by chromatography (gradient AcOEt/CH2Cl2 0:1 to 2:8, then CH2Cl2/MeOH 9:1) to give 1.8 g (34%) of the title product 86 as a colorless oil: m/z=234 (M+H)+.

Provenance & Evidence