Hydrochloric Acid → N-[[4-(1,1-Dimethylethyl)phenyl]methyl]-3-methoxybenzeneethanamine

Participants

Reaction Steps

0.38 ml of 4-tert-butylbenzaldehyde (2.25 mmol) and 0.22 ml of 2-(3-methoxy-phenyl)-ethylamine (1.5 mmol) were dissolved in 5 ml methanol at rt and then refluxed for 2 h. After cooling down to rt, 85 mg (2.25 mmol) of sodium borohydride were added in portions and the reaction mixture was then refluxed for 3 h. After cooling down to rt, the reaction mixture was treated with 0.15 ml 1 N HCl and concentrated in vacuo. The residue was diluted with water/EtOAc. After separation of the organic phase, the aqueous phase was extracted with EtOAc and the combined organic phases were washed with brine, dried with magnesium sulfate, filtered off and concentrated in vacuo. The residue was purified by column chromatography (90 g silica gel; EtOAc/heptane 1:1) to give 520 mg light yellow oil (>100%).

Provenance & Evidence