Dibenzylamine → HCID 66774767, compound

Participants

Reaction Conditions

Reaction Steps

A solution of ethyl 2-methyl-4-oxopiperidine-1-carboxylate (2.20 grams, 11.9 mmol) and benzyl benzylamine in dichloroethane/methanol (4:1, 50 mL) was heated over 3 Å molecular sieves at 90° C. for 16 hours. The reaction mixture was cooled to 0° C., and sodium triacetoxy borohydride (5.03 g, 23.8 mmol) was added. The resulting reaction mixture was stirred at room temperature for 30 minutes and then was filtered through a 0.45 μm membrane and concentrated to dryness under reduced pressure. The residue was taken up in aqueous 1N HCl solution and washed with ether (2×50 mL). The pH of the aqueous phase was adjusted to a pH of approximately 7 with 1M aqueous sodium bicarbonate solution. The aqueous phase was back extracted twice with ether (4×50 mL) and the combined organic phases were dried over sodium sulfate and concentrated under reduced pressure. Chromatography on silica gel with dichloromethane/methanol (94:6) gave 1.57 g (47% yield) of a yellow oil.

Provenance & Evidence