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

Participants

Reaction Steps

To a solution of trifluoro-methanesulfonic acid 4-[1-cyclopropylmethyl-3-(3-methoxy-phenyl)-piperidin-3-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 of 1-cyclopropylmethyl-3-(3-methoxy-phenyl)-3-(4-thiophen-2-yl-phenyl)-piperidine. 1HNMR (400 MHz, CDCl3) δ 749 (d, 2H), 7.35 (d, 2H), 7.22-7.06 (comp, 3H), 7.05-7.00 (m, 1H), 6.96 (s, 1H), 6.89 (d, 1H), 6.70-6.67 (m, 1H), 3.76 (m, 3H), 3.17-2.82 (comp, 2H), 2.61-2.39 (comp, 2H), 2.27-2.18 (comp, 4H), 1.62-1.39 (comp, 3H), 0.60-0.45 (comp, 2H), 0.18-0.11 (comp, 2H); MS (M+1) 404.2.

Provenance & Evidence