Thionyl Chloride → HCID 18966440, compound

Participants

Reaction Steps

By the procedure described in Example 5, thionyl chloride (2.38 ml, 32.7 mmol) and 3-hydroxy-3-(4-pyridinyl)-1-azabicyclo[2.2.2]octane (3.34 g, 15.4 mmol, prepared as in Example 10a) gave 0.11 g of 3-chloro-3-(4-pyridinyl)-1-azabicyclo[2.2.2]octane dihydrochloride; m.p. 165°-170° C.; Found: C, 46.78; H, 5.97; N, 8.77. C12H17N2Cl3.0.75H2O requires C, 46.62; H, 6.03; N, 9.06; δ(360 MHz, D2O) 8.882 (2H, d, J= 7.0 Hz, py-H), 8.231 (2H, d, J=7.9 Hz, py-H), 4.38 (2H, m, H2 -2), 3.70-3.15 (4H, m, H2 -6 and H2 -7), 2.75-1.60 (5H, m, H-4, H2 -5 and H2 -8); m/e 222 (M+), and 1.29 g of 3-(4-pyridinyl)-1-azabicyclo[2.2.2]oct-2-ene dihydrochloride; m.p. 245°-250° C.; Found: C, 55.40; H, 6.19; N, 10.68. C12H16N2Cl2.0.05H2O requires C, 55.41; H, 6.24; N, 10.77; δ(360 MHz, D2O) 8.814 (2H, d, J=6.9 Hz, py-H), 8.171 (2H, d, J=6.9 Hz, py-H), 7.529 (1H, d, J=1.4 Hz, H-2), 3.73 and 3.27 (5H, m, H-4, H2 -6 and H2 -7), 2.25 and 1.93 (4H, m, H2 -5 and H2 -8); m/e 186 (M+).

Provenance & Evidence