Ethyl Acetate → HCID 67366133, compound

Participants

Reaction Steps

60 g (3.5 equiv.) of Cbz chloride were added dropwise over a period of 10 minutes to a solution of 33 g (1 equiv.) of 1-benzyl-4-phenyl-4-(pyrrolidin-1-yl)piperidine in 330 ml of chloroform, and the resulting reaction mixture was stirred for 30 minutes at room temperature. The progress of the reaction was monitored by thin-layer chromatography (ethyl acetate). When the reaction was complete, the solvent was distilled off completely and the residue was adjusted to ˜pH 6 with 10% HCl solution and washed 3× with 100 ml of EtOAc. In an ice bath, the aqueous solution was adjusted to ˜pH 9 with NaOH solution and then extracted 3× with 100 ml of chloroform. 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; 20% EtOAc/heptane). 11 g (29%) of product were obtained in the form of a yellow solid.

Provenance & Evidence