Sodium hydride → Tert-butyl [4-[2-(benzimidazol-2-yloxy)ethyl]piperazin-1-yl] carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl 4-(2-hydroxyethyl)-1-piperazinecarboxylate (230 mg, 1.00 mmol) in DMF (2 ml) was added sodium hydride (55%, 52 mg, 1.19 mmol) with ice-cooling and stirred at 75° C. for 30 minutes, and then added 1-benzyl-2-chlorobenzimidazole (243 mg, 1.00 mmol) and stirred at 75° C. for 24 hours. The reaction solution was concentrated in vacuo, and the resulting residue was dissolved in chloroform. The organic layer was washed with water and a saturated sodium chloride solution successively, dried over anhydrous sodium sulfate and concentrated in vacuo. The resulting residue was purified by a silica gel column chromatography (silica gel 25 g, developing solvent; hexane:ethyl acetate=5:1 1:1) to provide 369 mg (yield 85%) of tert-butyl [4-[2-(benzimidazol-2-yloxy)ethyl]piperazin-1-yl]carboxylate as colorless solid.

Provenance & Evidence