Hydrochloric Acid → GT-2227

Participants

Reaction Conditions

Reaction Steps

1-[1-Triphenylmethyl-1H-imidazol-4-yl]-6-cyclohexyl-cis-3-hexene (1 gram, 2.12 mmol) was dissolved in ethanol (20 ml). 2N HCl (60 ml) was added and the mixture heated at 90° C. for 1 hour. The reaction mixture was cooled, filtered and the filtrate neutralized with 10% NaOH solution and then partitioned between CHCl3 and water. The chloroform layer was separated, dried over Na2SO4, filtered and evaporated in vacuo to obtain the crude oil. The crude product was purified by silica gel column chromatography using MeOH/CHCl3, (10:90) to afford 475 mgs of 1-[1H-imidazol-4-yl]-6-cyclohexyl-cis-3-hexene (24). ##STR55## 4-(6-Cyclohexyl-cis-3-enyl)imidazole (24) 1H-NMR (300 MHz, CDCl3): δ7.52 (s, 1H), 6.76 (s, 1H), 5.38 (m, 2H), 2.65 (m, 2H), 2.36 (m, 2H), 1.98 (m, 2H), 1.64 (m, 5H), 1.22 -1.08 (m, 6H), 0.84 (m, 2H); Mass Spectrum (DCl/NH3): 233 (M+1)+, MW=232.3704, C15H24N2 ; CNH Analysis: Calc.: C: 77.58, H: 10.34, N: 12.06; Found: C: 76.14, H: 10.04, N: 11.95.

Provenance & Evidence