反应详情

To a solution of 7.84 g (30.0 mmoles) ethyl 1-benzoyl-4-piperidinecarboxylate (G. R. Clemo and E. Hoggarth, J. Chem. Soc., 41, (1941) in 60 ml dry tetrahydrofuran at -78° C. under argon was added dropwise over 10 minutes 33.0 ml (33.0 mmoles) lithium bis(trimethylsilyl)amide in tetrahydrofuran and the resulting solution was stirred 30 minutes. To this solution was added dropwise over 2 minutes 5.64 g (33.0 mmoles) benzyl bromide in 10 ml dry tetrahydrofuran and the resulting solution was stirred overnight while warming from -78° C. to room temperature. The reaction was quenched with 20 ml saturated ammonium chloride solution and extracted with 2×100 ml ethyl acetate. The combined extracts were washed with 20 ml water and brine, dried, and the solvent removed in vacuo to give an oil. The oil was stirred under 25 ml hexane at -15° C., the hexane was decanted and the oil was dried in vacuo to give 12.5 g crude product as a viscous oil;

1. stirringthe resulting solution was stirred overnight
2. temperaturewhile warming from -78° C. to room temperature
3. customThe reaction was quenched with 20 ml saturated ammonium chloride solution
4. extractionextracted with 2×100 ml ethyl acetate
5. washThe combined extracts were washed with 20 ml water and brine
6. customdried
7. customthe solvent removed in vacuo
8. customto give an oil
9. stirringThe oil was stirred under 25 ml hexane at -15° C.
10. customthe hexane was decanted
11. customthe oil was dried in vacuo