Sodium hydride → (1-(3-carboethoxypropyl)-1H-benzimidazol-2-yl)(1-(t-butoxycarbonyl)piperidin-4-yl)amine

Participants

Reaction Conditions

Reaction Steps

Combine (1H-benzimidazol-2-yl)(1-(t-butoxycarbonyl)piperidin-4-yl)amine (0.51 g, 1.61 mmol) and dimethylformamide (15 mL). Add sodium hydride (0.086 g, 60% in oil, 2.15 mmol). Heat to 80° C. After 15 minutes, add ethyl 4-bromobutyrate (0.35 mL, 2.45 mmol) and continue heating at 80° C. After 18 hours, cool and partition the reaction mixture between dichloromethane and a saturated aqueous sodium bicarbonate solution. Separate the layers and extract the organic layer with brine. Dry the organic layer over MgSO4, filter, and concentrate in vacuo to give (1-(3-carboethoxypropyl)-1H-benzimidazol-2-yl)(1-(t-butoxycarbonyl)piperidin-4-yl)amine.

Provenance & Evidence