Potassium Carbonate → 3-(4-benzylpiperidin-1-yl)-N-(2-tert-butoxybenzyl)-N-(pyridin-2-ylmethyl)propan-1-amine

Participants

Reaction Steps

The same procedure as described for compound 20 was applied to 4-benzyl piperidin (0.30 g, 1.73 mmol), compound 19 (0.4 g, 1.15 mmol), KI (0.57 g, 3.45 mmol) and K2CO3 (0.79 g, 5.75 mmol). The residue was redissolved in CH2Cl2 and chromatographed on a silica-gel column with the following eluents: 5% methanolic NH3 (7 M NH3 in methanol/95% CH2Cl2. The product was isolated as yellow oil (64% yield). 1H NMR (CDCl3) δ 8.453 (dd, 1H, Ar), 7.576 (ddd, 1H, Ar), 7.516 (m, 2H, Ar), 7.224 (m, 2H, Ar), 7.135 (m, 1H, Ar), 7.075 (m, 4H, Ar), 6.982 (m, 2H, Ar), 3.730 (s, 2H, —CH2—), 3.655 (s, 2H, —CH2—), 2.864 (d, 2H, —CH2—), 2.482 (t, 4H, —CH2—CH2—), 2.324 (t, 2H, —CH2—), 1.888 (t, 2H, —CH2—), 1.728 (p, 2H, —CH2—), 1.586 (d, 2H, —CH2—), 1.502 (m, 1H, —CH—), 1.324 (s, 9H, —C(CH3)3), 1.288 (overlapped m, 2H, —CH2—). Mass Spec.=486.35 (M+H)+.

Provenance & Evidence