Hydrochloric Acid → (E)-2-[2-(Cyclohexyl)ethenyl]-5-methoxy-1-(2-pyridyl)-1H-benzimidazole hydrochloride

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Reaction Steps

Free base of the titled compound was prepared from 4-methoxy-2-amino-N-(2-pyridyl)aniline and (E)-3-Cyclohexylacryloyl chloride according to the preparation of (E)-1-(2-pyridyl)-2-styryl-1H-benzimidazole (Example 1, method A). The free base was dissolved with a 10% methanol solution of hydrogen chloride (5 ml). Concentration and recrystallization from ethyl acetate-hexane yielded the titled compound. MW: 369.90; mp: 168.0-169.0° C.; 1H-NMR (DMSO) δ: 8.80-8.76 (1H, m), 8.24 (1H, td, J=7.7, 1.8 Hz), 7.82-7.71 (2H, m), 7.46 (1H, d, J=9.2 Hz), 7.34-7.25 (2H, m), 7.09 (1H, dd, J=9.2, 2.6 Hz), 6.42 (1H, dd, J=15.8, 1.1 Hz), 3.56 (3H, s), 2.40-2.20 (1H, m), 1.80-1.55 (5H, m), 1.40-1.05 (5H, m).

Provenance & Evidence