Dichloromethane → HCID 10205057, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 0.33 mL (3.05 mmol) of 1-aminopiperidine in 2 mL of dry toluene under N2, 1.5 mL (3.05 mmol) of 2M trimethylaluminum in hexane was added with cooling in ice bath. The cold bath was removed, reaction was stirred for 1 h and 0.5 g (1.22 mmol) of ethyl 4-(2,4-dichlorophenyl)-5-(4-chlorophenyl)-1-methylimidazole-2-carboxylate in 3 mL of toluene, and 1.5 mL of CH2Cl2 was added. The mixture was heated in a 60° C. bath for 2 h, cooled, quenched with water and the pH was adjusted to 5 with 1.2 N HCl. The solution was extracted with EtOAc twice. The combined EtOAc layer was washed with brine, dried and concentrated. The residue was purified by flash chromatography using 30% EtOAc/hexane as an eluant to isolate the title compound. 1H NMR (500 MHz, CDCl3): δ 1.47 (m, 2H), 1.77–1.82 (m, 4H), 2.89 (s, 4H), 4.00 (s, 3H), 7.11–7.14 (m, 2H), 7.23–7.26 (m, 1H), 7.28–7.30 (m, 1H), 7.36–7.39 (m, 3H), 8.15 (s, 1H). LC-MS: Rt=3.6 min. m/e=465.1 (M+1).

Provenance & Evidence