Fumaric Acid → 3-[(4'-Nitro-1,1'-biphenyl-4-yl)oxy]quinuclidine hemifumarate

Participants

Reaction Steps

The product of Example 5A (33 mg, 0.1 mmol) in ethyl acetate/ethanol (3 mL, 1:1) was treated with fumaric acid (12 mg, 0.1 mmol) at ambient temperature for 10 hours. The title compound was obtained as a solid (14 mg, yield, 36%). 1H NMR (MeOH-d4, 300 MHz) δ 1.70-1.83 (m, 1H), 1.85-2.09 (m, 2H), 2.17-2.30 (m, 1H), 2.39-2.47 (m, 1H), 3.06-3.35 (m, 5H), 3.60-3.72 (m, 1H), 6.67 (s, 1H), 7.09 (dt, J=8.8, 2.5 Hz, 2H), 7.70 (dt, J=9.2, 2.3 Hz, 2H), 7.83 (dt, J=8.8, 2.4 Hz, 2H), 8.29 (dt, J=8.8, 2.3 Hz, 2H) ppm. MS (Cl/NH3): m/z 325 (M+H)+. Anal. Calculated for C19H20N2O3.0.5C4H4O4.0.35H2O: C, 64.89; H, 5.89; N, 7.21. Found: C, 64.82; H, 6.02; N, 6.95.

Provenance & Evidence