Benzophenone imine → HCID 86670013, compound

Participants

Reaction Conditions

Reaction Steps

To a degassed solution of 4-benzyl-6-(4-bromo-phenyl)-morpholine (4.00 g; 12.04 mmol) in toluene (50 mL) was added benzophenone imine (2.42 mL; 14.45 mmol), 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.60 g; 0.96 mmol), tris-(dibenzylideneacetone)-dipalladium(0) (0.22 g; 0.24 mmol) and NaOtBu (1.62 g; 16.86 mmol). The resulting mixture was heated to 100° C. for 16 hours. After cooling to RT a 5% aqueous NaHCO3 solution was added, and the product was extracted with EtOAc. The combined organic layers were dried (Na2SO4), filtered, and concentrated in vacuo. The residue was purified by column chromatography (SiO2, Et2O:hexanes 1:1) to afford benzhydrylidene-[4-(4-benzyl-morpholin-2-yl)-phenyl]-amine (3.30 g).

Provenance & Evidence