Triethylamine → HCID 21472416, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-ethynyl-3-hydroxyquinuclidine (302 mg), 4-iodoacetanilide (522 mg), bis(triphenylphosphine)-palladium (II) chloride (70 mg), copper (I) iodide (35 mg), triethylamine (2 ml) and DMF (4 ml) was heated at 65° C. under an atmosphere of argon for 4 hours. The reaction mixture was cooled then poured into 5% sodium carbonate solution (10 ml) and the resulting mixture extracted with ethyl acetate (3×5 ml). The organic extracts were combined, dried (MgSO4) and evaporated to give a solid residue. This residue was purified by flash column chromatography using a mixture of 10% methanol in dichloromethane containing 1% 0.880 ammonia as eluent to give 3-[2-(4-acetamidophenyl)ethynyl]-3-hydroxyquinuclidine (180 mg), m.p. 198° to 205° C. (with decomposition); microanalysis, found: C, 67.9; H, 7.0; N, 9.5%; C17H20N2O2.H2O requires: C, 67.55; H, 7.28; N, 9.27%; NMR (DMSO-d6): 1.3-1.45(1H, m), 1.56-1.7(1H, m), 1.8-2.0(3H, m), 2.06(3H, s), 2.7-2.8(4H, t), 2.85-2.92(1H, d), 3.1-3.17(1H, d), 5.65(1H, s), 7.3-7.35(2H, d), 7.55-7.6(2H, d) and 10.1(1H, br); m/Z 285 (M+H).

Provenance & Evidence