To a suspension of 4-phenylpiperidine-4-carbonitrile hydrochloride (6.7 mmol) in toluene (30 mL) are successively added bromobenzene (8.0 mmol), sodium tert-butoxide (17 mmol), tri-o-tolylphosphine (1.3 mmol), and tris(dibenzylideneacetone)dipalladium (0.7 mmol), then the mixture is refluxed for 20 h. The reaction mixture is cooled, diluted with water, then extracted with AcOEt. The organic extracts are washed with water and brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue is purified by silica gel column chromatography to give the title compound; 1H NMR (CDCl3) δ: 2.12-2.20 (2H, m), 2.23-2.28 (2H, m), 2.94-3.01 (2H, m), 3.86 (2H, d), 6.83 (1H, t), 7.04 (2H, d), 7.22-7.28 (2H, m), 7.36-7.41 (1H, m), 7.45-7.49 (2H, m), 7.56-7.59 (2H, m).
