Cyanogen bromide (3.0M in CH2Cl2, 0.1 mL, 0.3 mmol) was added dropwise to a mixture of 4-({[4′-(methylsulfonyl)-4-biphenylyl]oxy}methyl)piperidine hydrochloride (prepared as in Example 2, Step 1, 100 mg, 0.3 mmol) and triethylamine (0.083 mL, 0.6 mmol) in CH2Cl2 (5 mL) at ambient temperature. The reaction mixture was stirred at ambient temperature for 1 h and concentrated. The crude product was purified by chromatography on a silica gel column using 0 to 5% MeOH/CH2Cl2 to give 60 mg (54%) of 4-({[4′-(methylsulfonyl)-4-biphenylyl]oxy}methyl)-1-piperidinecarbonitrile as a white solid. 1H NMR (400 MHz, CDCl3): δ 7.97 (d, 2H, J=8.4 Hz), 7.72 (d, 2H, J=8.6 Hz), 7.55 (d, 2H, J=8.8 Hz), 6.98 (d, 2H, J=8.6 Hz), 3.87 (d, 2H, J=6.2 Hz), 3.58-3.47 (m, 2H), 3.08 (s, 3H), 1.96-1.86 (m, 2H), 1.53 (bs, 5H); LRMS (ESI), m/z 393 (M+Na).
