Hydrochloric Acid → HCID 3249029, compound

Participants

Reaction Steps

0.753 ml of 4-tert-butylbenzaldehyde (4.5 mmol) and 0.436 ml of 2-(2,4-dichloro-phenyl)-ethylamine (3 mmol) were dissolved in 8 ml methanol at rt and after 30 min at rt refluxed for 3.5 h. After cooling down to rt, 170 mg (4.5 mmol) of sodium borohydride were added in portions and the reaction mixture was then refluxed overnight. After cooling down to rt, the reaction mixture was treated with 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 (40 g silica gel; EtOAc/heptane 1:2) to give 691 mg colorless oil (68%). MS(ISP) 336.3 (M+H)+.

Provenance & Evidence