Hydrochloric Acid → 3-[4-(thien-3-yloxy)phenoxy]quinuclidine Hydrochloride

Participants

Reaction Steps

The product of Example 15E (40 mg, 0.13 mmol) in ethyl acetate (4 mL) was treated with 4M HCl in 1,4-dioxane (0.2 mL, 0.8 mmol). The title compound was obtained as a solid (26 mg, yield, 59%). 1H NMR (MeOH-d4, 300 MHz) δ 1.80–2.10 (m, 3H), 2.25–2.46 (m, 1H), 2.56 (m, 1H), 3.30–3.50 (m, 5H), 3.80 (m, 1H), 4.85 (m, 1H), 6.55 (dd, J=3.4, 1.7 Hz, 1H), 6.81 (dd, J=5.5, 1.7 Hz, 1H), 6.97 (dt, J=9.5, 3.0 Hz, 2H), 7.02 (dt, J=9.5, 3.1 Hz, 2H), 7.34 (dd, J=5.1, 3.1 Hz, 1H) ppm. MS (DCl/NH3) m/z 302 (M+H)+. Anal. Calculated for C17H19NO2S.1.0HCl.0.5H2O: C, 58.86; H, 6.10; N, 4.04. Found: C, 59.08; H, 5.88; N, 4.06.

Provenance & Evidence