Fumaric Acid → N-1-azabicyclo[2.2.2]oct-3-yl-1,1'-biphenyl-4,4'-diamine Fumarate

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The product of Example 24A (150 mg, 0.51 mmol) was treated with fumaric acid (Aldrich, 70 mg, 0.6 mmol) in ethyl acetate/methanol (10:1, 20 mL) at ambient temperature for 10 hours. The title compound was obtained as a solid (210 mg, yield, 99%): 1H NMR (MeOH-d4, 300 MHz) δ 1.81-1.92 (m, 1H), 2.02-2.15 (m, 2H), 2.22-2.35 (m, 2H), 3.02 (ddd, J=12.5, 4.7, 1.7 Hz, 1H) 3.24-3.44 (m, 4H), 3.77 (ddd, J=12.9, 9.2, 2.4 Hz, 1H), 3.90-4.02 (m, 1H), 6.64-6.72 (m, 4H), 6.81-6.90(m, 2H), 6.96-7.01 (m, 2H), 7.08-7.14 (m, 2H) ppm. MS (DCl/NH3) m/z 294 (M+H)+. Anal. Calculated for C19H23N3.1.2C4H4O4.0.3H2O: C, 65.25; H, 6.53; N, 9.59. Found: C, 65.20; H, 6.23; N, 9.28.

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