Dimethylformamide → HCID 86635668, compound

Participants

Reaction Steps

POCl3 (26.35 g, 16.06 ml, 1.6 eq.) was added dropwise to DMF (16.4 ml, 2 eq.) at 0-5° C. To the mixture was added dichloromethane (50 ml) in a dropwise fashion and it was stirred for 2 h at room temperature. A solution of benzyl 4-oxopiperidine-1-carboxylate (25 g, 0.10 mol) in dichloromethane (200 ml) was added dropwise to the mixture and it was stirred for 2 h at room temperature. Progress of the reaction was monitored by TLC (30% ethyl acetate/hexane). Upon completion of the reaction the mixture was poured into crushed ice and basified to a pH˜8 with sodium carbonate. Then the dichloromethane layer was separated and the aqueous layer was extracted with dichloromethane (2×200 ml). The combined organic layers were dried over sodium sulfate, concentrated under reduced pressure and the crude product obtained was purified by column chromatography (silica, 8% ethyl acetate/hexane). Yield: 14.5 g (48%).

Provenance & Evidence