1-Chloroethyl chloroformate → 4-(Azetidin-3-yloxy)-1-benzyl-1,3-dihydro-benzoimidazol-2-one

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Reaction Conditions

Reaction Steps

4-(1-Benzhydryl-azetidin-3-yloxy)-1-benzyl-1,3-dihydro-benzoimidazol-2-one (78 mg, 0.17 mmol) was dissolved in 0.33 mL dichloroethane and cooled to 0° C. under nitrogen. α-Chloroethyl chloroformate (0.018 mL, 0.164 mmol) was added dropwise, and the solution was refluxed for 2 hours, concentrated in vacuo, and dissolved in 20 mL methanol. The solution was refluxed for one hour, concentrated in vacuo and dissolved in 75 mL dichloromethane, and the resulting solution was washed with 75 mL 2M aqueous potassium carbonate and 75 mL water. The organic phase was dried over sodium sulfate, concentrated in vacuo and purified by flash (3% methanol in dichloromethane) chromatography to give 42 mg (0.14 mmol, 82%) of 4-(azetidin-3-yloxy)-1-benzyl-1,3-dihydro-benzoimidazol-2-one as a clear oil. MS: 296 (M+H)+. The corresponding hydrochloride salt, prepared by recrystallization from EtOH/HCl, gave a melting point of 181.0-184.0° C.

Provenance & Evidence