2-(Dimethylamino)ethanol → HCID 67740218, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-[2-(2-allyl-4-methoxycarbonylphenyl)ethynyl]quinuclidin-3-ol (0.64 g), sodium cyanide (50 mg) and N,N-dimethylethanolamine (10 ml) was heated at 90° C. for 24 hours. The mixture was evaporated to give an oil which was partitioned between ethyl acetate and water. The organic phase was separated, washed with brine, dried (MgSO4) and evaporated. The residue was purified by flash column chromatography on silica gel using 10% methanol in dichloromethane containing 1% ammonia (density 0.88 g/cm3) as eluent to give 3-[2-(2-allyl-4-(2-(N,N-dimethylamino)ethoxycarbonyl)phenyl)ethynyl]quinuclidin-3-ol as a gum (0.559 g); microanalysis found: C, 66.7; H, 7.6; N, 6.7%, C23H30N2O3.0.4CH2Cl2.0.1 H2O requires 7.47; N, 6.7%; NMR (CDCl3): 1.32-1.55(1H, m), 1.55-1.88(1H, m), 1.88-2.20(3H, m), 2.33(6H, s), 2.70(2H, t), 2.65-3.15(4H, m), 3.07(1H, d), 3.33(1H, dd), 3.56(2H, d), 4.41(2H, t), 4.98-5.15(2H, m), 5.29(CH2Cl2), 5.85-6.10(1H, m), 7.43(1H, d) and 7.71-7.90(2H, m); m/Z 383 (M+H).

Provenance & Evidence