Hydrochloric Acid → HCID 178420888, compound

Participants

Reaction Conditions

Reaction Steps

1-[1-Triphenylmethyl-1H-imidazol-4-yl]-6-cyclohexyl-3-hexyne (0.629 g, 1.33 mmol) was suspended in ethyl alcohol (3 ml). 2N HCl (25 ml) was added and the reaction mixture heated at 90° C. for 1 hr. The reaction mixture was cooled, filtered through a pad of celite and the filtrate evaporated in vacuo. The residue was dissolved in methanol (20 ml). 10% Pd(C) (0.139 g) and ammonium formate (1.5 g) were added, and the reaction mixture heated at 65° C. under N2 for 6.5 hours. The reaction mixture was cooled, filtered through a pad of celite and the methanol filtrate concentrated. The residue was partitioned between CH2Cl2 and 10% NaOH solution (100 ml, 1:1). The CH2Cl2 layer was separated, washed with water (50 ml), dried over MgSO4, filtered and evaporated in vacuo. Purification by flash chromatography using ethyl acetate as eluent gave 108 mgs of final product. ##STR72## 4-(6-Cyclohexylhexyl)imidazole (41) 1H-NMR (300 MHz, CD3OD): δ7.53 (s, 1H), 6.73 (s, 1H), 2.56 (t, J=7.5 Hz, 2H), 1.65 (m, 7H), 1.40-1.10 (m, 12H), 0.89 (m, 2H); Mass Spectrum: (DCl/NH3): 235 (M+1)+.

Provenance & Evidence