Benzophenone imine → HCID 86607828, compound

Participants

Reaction Steps

Heat a mixture of 4-(3-bromo-2-fluoro-phenoxy)-1-methyl-piperidine (preparation 18 or 19, 1.60 g), benzhydrylideneamine (1.21 g), tris(dibenzylidineacetone)-dipalladium(0) (0.11 g), racemic-2,2′-bis(diphenylphosphino)-1,1′binaphthyl (0.138 g) and sodium t-butoxide (0.75 g) in toluene (100 mL) and reflux. After 3 hr., cool to room temperature, load on a SCX column (10 g), wash with methanol, elute the product with 2 M NH3 in methanol. Evaporate the NH3-methanol solution and purify on a 35 g silica gel column eluting with dichloromethane-2M NH3 in methanol, gradient to give benzhydrylidene-[2-fluoro-3-(1-methyl-piperidin-4-yloxy)-phenyl]-amine. Dissolve the amine in THF and add 1N HCl. After 10 min., basify with NH4OH and partition between ethyl acetate and saturated aqueous NaCl, dry over sodium sulfate, evaporate and purify on a 35 g silica gel column eluting with: dichloromethane-2M NH3 in methanol, gradient) to give the title compound (1.19 g): mass spectrum (electric spray) m/z=225 (M+1); 1H NMR (CDCl3): 6.78 (m, 1H), 6.38 (m, 2H), 4.25 (m, 1H), 3.73 (br s, 2H), 2.69 (m, 2H), 2.27 (s, 3H), 2.26 (m, 2H), 1.97 (m, 2H), 1.87 (m, 2H).

Provenance & Evidence