1-Chloroethyl chloroformate → 5-methyl-3H-spiro[1-benzofuran-2,4'-piperidine]

Participants

Reaction Steps

To a solution of 1′-benzyl-5-methyl-3H-spiro[1-benzofuran-2,4′-piperidine](0.12 g, 0.41 mol) in dichloromethane (3 ml) was added 1-chloroethyl chloroformate (87 mg, 0.61 mmol). The solution was stirred at room temperature overnight. The solvent was removed i. vacuo. The residue was dissolved in methanol (3 ml), and the solution was heated at 70° C. for 2 h. The solvent was eeporated, and the residue treated with diethyl ether. The precipitate formed was collected by filtration, washed with diethyl ether, and dissolved in methanol (1 ml). Water (25 ml) was added, and pH was adjusted to 10 by addition of 2 M aq. NaOH. The mixture was extracted with dichloromethane (2×25 ml), and the combined organic extracts were dried over Na2SO4. Evaporation of solvent afforded brownish oil (64 mg, 77%).

Provenance & Evidence