Ethyl Acetate → 4-[3-(5-(1,2,4-Triazol-4-yl)-1H-indol-3-yl)propyl]-1-(alpha-methoxycarbonylbenzyl)piperidine

Participants

Reaction Conditions

Reaction Steps

4-[3-(5-(1,2,4-Triazol-4-yl)-1H-indol-3-yl)propyl]piperidine (Description 2, 0.800 g, 0.0026 mol) was dissolved in anhydrous DMF (10 ml), under N2, and potassium carbonate (0.540 g, 0.0039 mol) added followed by (±)-methyl α-bromophenylacetate (Aldrich, 0.5 ml, 0.0031 mol). The reaction was stirred at 25° C. for 16 h, then poured into ethyl acetate (100 ml) and H2O (30 ml). The organic layer was collected, washed with H2O (3×30 ml), dried over MgSO4 and evaporated with 1-5% MeOH/CH2Cl2 to obtain the title compound as a colourless oil. 1H NMR 1.23-1.33 (6H, m), 1.66 (5H, m), 2.04 (1H, br m), 2.72 (2H, t, J=3 Hz), 2.96 (1H, bm), 3.69 (3H, s), 3.98 (1H, br s), 7.11 (1H, d, J=1 Hz), 7.14 (1H, d, J=2 Hz), 7.33 (3H, m), 7.43-7.48 (2H, m), 7.50 (1H, d, J=3 Hz), 7.51 (1H, d, J=1 Hz), 8.07 (br s, indole (NH)), 8.45 (2H, s, Ar (triazole)).

Provenance & Evidence