Reaction Steps
The compound 15 (1.9 g, 4.46 mmol), 4-phenylpiperidine (1.128 g, 6.99 mmol) and K2CO3 (0.64 g, 4.66 mmol) were added to 50 mL CH3CN, and the solution was refluxed under argon atmosphere for 16 h. After cooling to room temperature, the solvent was evaporated to dryness. Purification was carried out on a silica gel TLC plate that was developed in 3% methanolic NH3 (7 M NH3 in methanol)/97% CH2Cl2. The product was obtained as pale yellow oil (73%). 1H NMR (CDCl3) δ 7.382 (d, 1H, Ar), 7.289 (m, 2H, Ar), 7.229 (m, 2H, Ar), 7.186 (m, 1H, Ar), 7.136 (m, 1H, Ar), 7.013 (m, 2H, Ar), 3.587 (s, 2H, —CH2—), 3.160 (m, 2H, —CH2—), 3.071 (d, 2H, —CH2—), 2.519 (overlapping m, 2H, —CH2—), 2.496 (overlapping m, 1H, —CH—), 2.419 (t, 2H, —CH2—), 2.355 (m, 2H, —CH2—), 2.045 (m, 2H, —CH2—), 1.837 (m, 4H, —CH2—CH2—), 1.525 (m, 2H, —CH2—), 1.472 (m, 2H, —CH2—), 1.437 (s, 9H, —C(CH3)3), 1.426 (s, 9H, —C(CH3)3), 1.280 (m, 4H, —CH2—CH2—). Mass Spec=566.43 (M+H)+.
