Acetic Acid → N-[(3-bromo-5-chlorophenyl)methyl]cyclopropanamine

Participants

Reaction Steps

To a 4:1 (v/v) MeOH:THF solution (0.06 M) of 3-bromo-5-chlorobenzaldehyde (1 eq.) and cyclopropylamine (1.1 eq.) was added sodium cyanoborohydride (1.5 eq.) portionwise followed by neat acetic acid (3 eq.). The resulting mixture was stirred at RT for 20 h. The volatiles were then removed in vacuo. The resulting residue was taken up in ether and sat. aq. NH4Cl. The aqueous layer was separated and back-extracted with ether. The combined organic extracts were then washed with brine, dried over MgSO4 and filtered. Concentration of the filtrate in vacuo afforded the crude title compound as a yellow oil.

Provenance & Evidence