Benzylamine → N-benzyl-3-fluoro-2-({[phenylmethyl]imino}methyl)aniline

Participants

Reaction Conditions

Reaction Steps

A resealable tube was charged with 2,6-difluorobenzaldehyde (7.11 g, 50 mmol), benzylamine (27.3 mL, 250 mmol), cesium carbonate (19.5 g, 60 mmol), and dry toluene (170 mL). The tube was sealed and heated at 150° C. for 4 hours with rapid stirring. The reaction mixture was cooled and partitioned between ethyl acetate and 10% aqueous HCl. The organic layer was removed and the aqueous layer was extracted (2×, ethyl acetate). The combined organic extracts were washed (2×, saturated sodium bicarbonate; 2×, brine), dried (Na2SO4), filtered and concentrated under vacuum to provide the title compound (13.17 g; 83%) which was used without purification. MS (DCI/NH3) m/e 318 (M+H)+.

Provenance & Evidence