Toluene → Benzhydrylidene-(3-(4-dimethylamino-cyclohex-1-enyl)-2-fluoro-phenyl)-amine

Participants

Reaction Steps

Combine (4-(3-bromo-2-fluoro-phenyl)-cyclohex-3-enyl)-dimethyl-amine (preparation 7, 1.70 g, 6.84 mmol), benzophenone imine (1.24 g, 6.84 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.104 g, 0.11 mmol), racemic BINAP (0.142 g, 0.228 mmol), and sodium t-butoxide (0.767 g, 0.8 mmol) with toluene (5 mL) and heat at reflux for 2 hr. Dissolve the reaction mixture in MeOH and filter through a SCX column (Bond Elut™, 10 g), wash with MeOH, elute the product with 2M NH3 in MeOH, evaporate the solvent, and further purify on a silica gel column (DCM:2M NH3 in MeOH, gradient) to give pure benzhydrylidene-(3-(4-dimethylamino-cyclohex-1-enyl)-2-fluoro-phenyl)-amine (2.39 g): MS (ES): m/z=399 (M+H)+. 1H NMR (CDCl3): δ 7.76 (m, 2H), 7.46 (m, 1H), 7.40 (m, 2H), 7.25 (m, 4H), 7.13 (m, 2H), 6.85 (m, 1H), 6.73 (m, 1H), 6.65 (m, 1H), 5.70 (m, 1H), 3.05 (m, 1H), 2.61 (s, 6H), 2.6-2.2 (m, 5H), 1.75 (m, 1H).

Provenance & Evidence