Water → (1-(5-(ethoxycarbonyl)fur-2-ylmethyl)-1H-benzimidazol-2-yl)(1-ethoxycarbonylpiperidin-4-yl)amine

Participants

Reaction Conditions

Reaction Steps

Combine (1H-benzimidazol-2-yl)(1-ethoxycarbonyl-piperidin-4-yl)amine (10.94 g, 37.9 mmol), sodium carbonate (6.03 g, 57 mmol), and ethyl 5-chloromethyl-2-furoate (12.88 g, 68.3 mmol) in dimethylformamide (115 mL). Heat at about 70° C. After 18 hours, cool the reaction mixture and pour into water. Extract four times with 2/1 ethyl acetate/toluene. Combine the organic layers and extract with brine. Dry the combined organic layers over Na2SO4, filter, and concentrate in vacuo to obtain a residue. Chromatograph the residue on silica gel eluting with 20% acetone/dichloromethane. Combine the product containing fractions and evaporate in in vacuo to give a residue. Triturate the residue with diethyl ether to give a solid. Collect the solid by filtration, rinse with diethyl ether, and dry to give (1-(5-(ethoxycarbonyl)fur-2-ylmethyl)-1H-benzimidazol-2-yl)(1-ethoxycarbonylpiperidin-4-yl)amine. Recrystallization of an analytical sample (0.3 g) from ethyl acetate/hexane (about 1 mL/4 mL) gives (1-(5-(ethoxycarbonyl)fur-2-ylmethyl)-1H-benzimidazol-2-yl)(1-ethoxycarbonylpiperidin-4-yl)amine: mp; 133-135° C. Elemental Analysis calculated for C23H28N4O5: C 62.71; H 6.41; N 12.72; Found: C 62.69; H 6.29; N 12.66.

Provenance & Evidence