Benzyl chloroformate → HCID 67366402, compound

Participants

Reaction Steps

500 ml (10 equiv.) of Cbz chloride were added dropwise, over a period of 1 hour, to 50 g (1 equiv.) of 1-benzyl-N,N-dimethyl-4-phenylpiperidine-4-amine, and the resulting reaction mixture was stirred for 2 hours at room temperature. The progress of the reaction was monitored by thin-layer chromatography (10% MeOH/CHCl3). When the reaction was complete, the mixture was cooled to 0° C. and rendered basic with saturated sodium hydrogen carbonate solution, and the reaction mixture was extracted 3× with 300 ml of EtOAc. The combined organic phases were dried with Na2SO4. After removal of the solvent under reduced pressure, purification was carried out by column chromatography (silica gel; 50% EtOAc/heptane). 12 g (21%) of product were obtained in the form of an oil.

Provenance & Evidence