4-Iodoaniline → HCID 21072621, compound

Participants

Reaction Steps

3-Quinuclidinone hydrochloride (Aldrich, 3.22 g, 20 mmol) was treated with 4-iodo-aniline (2.19 g, 10 mmol) according to the procedure of Example 30A. The title product was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3.H2O, 90:10:2, Rf. 0.10) as oil (3.24 g, yield, 98%). 1H NMR (MeOH-d4, 300 MHz) δ 1.70–1.81 (m, 1H), 1.93–2.04 (m, 2H), 2.08–2.24 (m, 2H), 2.89 (ddd, J=12.9, 5.1, 2.7 Hz, 1H), 3.12–3.28 (m, 4H), 3.64 (ddd, J=12.9, 9.5, 2.4 Hz, 1H), 3.79–3.85 (m, 1H), 6.46 (dt, J=9.0, 2.7 Hz, 2H), 7.39 (dt, J=9.1, 2.7 Hz, 2H) ppm. MS (DCl/NH3) m/z 329 (M+H)+.

Provenance & Evidence