Br[CH2:2][C:3]#[N:4].[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[CH:10]=[CH:11][CH:12]=1.C([O-])([O-])=O.[K+].[K+]>CC#N>[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH:13]2[CH2:18][CH2:17][N:16]([CH2:2][C:3]#[N:4])[CH2:15][CH2:14]2)[CH:10]=[CH:11][CH:12]=1A mixture of bromoacetonitrile (0.70 mL, 10 mmol), 4-(3-methoxyphenyl)piperidine (1.74 g, 9.1 mmol) and K2CO3 (1.3 g) in MeCN was stirred at room temperature for 3 days. The reaction mixture was partitioned between CH2Cl2 and H2O, and the organic extract was dried (Na2SO4). The solvent was then removed in vacuo to afford [4-(3-methoxyphenyl)-1-piperidinyl]acetonitrile as an amber oil (2.03 g, 97%): MS (DCl) m/z 231 (MH+). Anal. Calcd. for C14H18N2O.0.5 H2O: C, 70.27; H, 8.00; N, 11.71. Found: C, 70.12; H, 7.67; N, 11.87.
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