Reaction Steps
The same procedure as described for compound 20 was applied to 4-benzylpiperidine (0.46 g, 2.63 mmol), compound 23 (0.7 g, 1.75 mmol), KI (0.87 g, 5.25 mmol) and K2CO3 (1.21 g, 8.75 mmol). The residue was purified on a silica gel TLC plate that was developed in 5% methanolic NH3 (7 M NH3 in methanol/95% CH2Cl2. The product was isolated as yellow oil (80% yield). 1H NMR (CDCl3) δ 7.373 (d, 1H, Ar), 7.264 (m, 2H, Ar), 7.176 (t, 1H, Ar), 7.137 (d, 2H, Ar), 7.137 (d, 2H, Ar), 7.108 (d, 1H, Ar), 7.021 (dd, 1H, Ar), 6.985 (t, 1H, Ar), 3.577 (s, 2H, —CH2—), 3.167 (d, 2H, —CH2—), 2.892 (d, 2H, —CH2—), 2.524 (d, 2H, —CH2—), 2.498 (t, 2H, —CH2—), 2.453 (t, 2H, —CH2—), 2.290 (t, 2H, —CH2—), 1.839 (t, 2H, —CH2—), 1.657 (m, 2H, —CH2—), 1.618 (d, 2H, —CH2—), 1.517 (m, 1H, —CH—), 1.426 (s, 9H, —C(CH3)3, 1.376 (s, 9H, —C(CH3)3, 1.329 (overlapped m, 4H). Mass Spec.=538.77 (M+H)+.
