Benzyl Bromide → Ethyl-1-benzoyl-4-(phenylmethyl)-4-piperidinecarboxylate

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Reaction Steps

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;

Provenance & Evidence