Piperidine → 2-Chloro-4-(4-phenoxyphenyl)-6-(piperidin-1-yl)nicotinonitrile

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Reaction Steps

A mixture of 2,6-dichloro-4-(4-phenoxyphenyl)nicotinonitrile (34 mg, 0.100 mmol, from Step 2 of Example 8), triethylamine (0.028 mL, 0.199 mmol), 0.5 M acetonitrile solution of piperidine (0.199 mL, 0.100 mmol) in acetonitrile (1 mL) was stirred at room temperature for 36 h to give a suspension. The white solid was collected by filtration, washed with cold methanol (1 mL), dried under vacuum to give 2-chloro-4-(4-phenoxyphenyl)-6-(piperidin-1-yl)nicotinonitrile (15 mg, 39% yield). 1H NMR (400 MHz, CDCl3) δ ppm 7.51 (2H, δ, J=8.53 Hz), 7.39 (2H, t, J=8.03 Hz), 7.18 (1H, t, J=7.40 Hz), 6.98-7.12 (4H, 6.45 (1H, s), 3.63-3.81 (4H, m), 1.62-1.90 (7H, m), 1.52-1.80 (6H, s), 1.58 (9H, s); MS (ES+) m/z: 390 (M+H); LC retention time: 4.293 min (analytical HPLC Method A).

Provenance & Evidence