p-Toluenesulfonic acid → 3-(3-Pyridinyl)-3,7-diazabicyclo[3.3.1]nonane bis(4-methylbenzenesulfonate)

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Reaction Steps

The product from Example 57A was treated with p-toluenesulfonic acid (2.0 eq) and the obtained solid recrystallized from ethanol/ether to provide the title compound (53% yield). 1H NMR (CD3OD, 300 MHz) δ 2.04 (m, 2H), 2.37 (s, 6H), 2.39 (m, 2H), 3.23 (m, 2H), 3.31 (m, 2H), 3.59 (bd, J=13.24 Hz, 2H), 4.04 (bd, 12.14 Hz, 2H), 7.23 (d, J=8.09 Hz, 4H), 7.67(d, J=8.09 Hz, 4H), 7.88 (dd, J=5.52, 8.83 Hz, 1H), 8.20-8.24(m, 2H), 8.50 (d, J=2.57 Hz, 1H); MS (DCI/NH3) m/z 204 (M+H)+; Anal. calculated for C12H17N3.2.2 TsOH.H2O C, 56.01; H, 6.04; N, 7.15. Found: C, 56.25; H, 6.10; N, 6.79.

Provenance & Evidence