Diethyl Ether → 1-(5-Cyclohexyl-pentyl)-3-phenylquinolinium iodide

Participants

Reaction Steps

A solution of Phenyl-quinolin-3-yl-amine (100 mg, 0.45 mmol) toluene (2 ml) and 5-iodo-pentyl-benzene (373 mg, 1.36 mmol) in a sealed pressure tube was stirred at 110° C. for 24 hours. The reaction mixture was cooled to room temperature, diluted with Et2O (15 ml) and the precipitated compound was filtered and washed with Et2O (3×20 ml). The crude product was purified on a chromatographic column using methanol as an eluent to yield a pure product as an orange solid (75 mg, mp 140-141° C.). 1H NMR (CD3OD): δ 1.42-1.56 (m, 2H), 1.66-178 (m, 2H), 2.04-2.18 (m, 2H), 2.58-2.68 (t, 2H, J=7.2 Hz), 4.88-5.04 (t, 2H, J=7.8 Hz), 7.08-7.24 (m, 6H), 7.14 (dd, 2H, J=0.9, 7.5 Hz), 7.40-7.44 (t, 2H, J=8.4 Hz), 7.76-7.84 (t, 1H, J=7.5 Hz), 7.86-7.94 (m, 1H), 8.08 (d, 1H, J=8.4 Hz), 8.30 (d, 1H, J=9.0 Hz), 8.46 (d, 1H, J=2.4 Hz), 9.04 (d, 1H, J=2.7 Hz). Anal Calcd for: C26H27IN2.1H2O: C, 60.92; H, 5.70; N, 5.47. Found: C, 60.79; H, 5.33; N, 6.38.

Provenance & Evidence