Hydrochloric Acid → HCID 58852362, compound

Participants

Reaction Conditions

Reaction Steps

Combine (4-(3-bromo-5-fluoro-phenyl)-cyclohex-3-enyl)-dimethyl-amine (10.8 g, 36.2 mmol), benzhydrylideneamine (7.88 g, 43.5 mmol), toluene (250 mL), BINAP (0.90 g, 1.44 mmol) and sodium t-butoxide (4.87 g, 50.7 mmol) and heat to 90° C. for 10 min. until homogeneous. Add tris(dibenzylideneacetone)dipalladium(0) (0.66 g, 0.72 mmol) and heat to 100° C. for 3 hr. Add 6M HCl solution (60 mL) carefully and continue to heat at 100° C. for 1 hr. Cool to ambient temperature and wash with ethyl acetate (2×100 mL). Basify the aqueous layer with 5N NaOH solution and extract with ethyl acetate (3×250 mL). Dry the organic layer over sodium sulfate, filter and concentrate. Purify the residue by flash chromatography (silica gel, 10% 2M NH3/MeOH in DCM) to obtain 3-(4-dimethylamino-cyclohex-1-enyl)-5-fluoro-phenylamine (2.84 g, 33.5%).

Provenance & Evidence