[C:1]1([CH2:7][NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:10][CH2:11][CH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1>C(#N)C>[CH:12]1([CH2:11][CH2:10][NH:8][CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:16][CH2:15][CH2:14][CH2:13]1Combine 10.7 g (0.1 mol) of benzenemethanamine and 17.7 g (0.1 mol) of (2-bromoethyl)cyclopentane in 100 mL of acetonitrile. Heat the mixture to reflux and follow the progress of the reaction by thin-layer chromatography on silica gel. At the completion of the reaction remove the solvent in vacuo and add 100 mL of saturated sodium bicarbonate solution. Extract the aqueous mixture with three 100 mL portions of diethyl ether. Dry the combined extracts over anhydrous sodium sulfate. Filter the drying agent and remove the solvent in vacuo to obtain the title compound.
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