Sodium Carbonate → 1-Benzyl-4-(3-methoxy-phenyl)-4-(4-thiophen-2-yl-phenyl)-piperidine

Participants

Reaction Steps

To a solution of trifluoro-methanesulfonic acid 4-[1-benzyl-4-(3-methoxy-phenyl)-piperidin-4-yl]-phenyl ester (0.1 g, 0.2 mmol) in ethanol (4.5 mL) and water (0.5 mL) was added 2-thiophene boronic acid (0.052 g, 0.5 mmol) and sodium carbonate (0.037 g, 0.29 mmol) and tetrakis tripheny;phosphine palladium (0.02 g, 0.18 mmol). The reaction mixture was heated to reflux for 2 hours. The mixture was then filtered and the filtrate was concentrated under vacuum. The residue was purified by flash chromatography with hexanes/EtOAc (3:1) to afford 0.08 g (92% yield) of 1-Benzyl-4-(3-methoxy-phenyl)-4-(4-thiophen-2-yl-phenyl)-piperidine. 1HNMR (400 MHz, CDCl3) δ 7.50 (d, 2H), 7.33-7.18 (comp, 10H), 7.07-7.00 (m, 1H), 6.89-6.63 (comp, 2H), 6.69 (d, 1H), 3.76 (s, 3H), 3.42 (s, 2H), 2.61-2.39 (comp, 8H); MS (M+1) 440.2.

Provenance & Evidence