hz 2h nch 2 3 35 3 51 m 6h nch 2 4 27 s 2h nch 2 ar 4 28 4 35 m 1h nchar 6 69 d j 9 hz 3h ar u2014 h 7 20 7 23 m 4h ar u2014 h 7 46 s 6h ar u2014 h to a solution of 1 07 g of 3 bromobenzonitrile 5 88 mmol in 15 ml dry toluene was added 1 2 ml of 4 amino n benzyl piperidine 5 89 mmol 293 mg racemic binap 0 47 mmol 215 mg tris dibenzylideneacetone dipalladium 0 0 23 mmol and 790 mg sodium tert butoxide 8 23 mmol the reaction was heated at 80 u00b0 c under a nitrogen atmosphere for 4 hours the reaction was cooled to room temperature and 2 26 g of n n diethyl 4 bromobenzamide 8 83 mmol and 790 mg of sodium tert butoxide 8 23 mmol were added and the reaction heated to reflux after 20 hours the solution was cooled to room temperature and the reaction diluted with ethyl acetate 50 ml and water 30 ml was added filtered through celite and then the organic layer was separated dried mgso 4 filtered and concentrated the residue was purified by flash chromatography to yield an oil 2 54 g 5 45 mmol 93 400 mhz cdcl 3 u03b4 h 1 36 br s 6h ch 3 1 44 1.