Benzyl Bromide → HCID 67329265, compound

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Reaction Steps

In a three-necked flask, under a azote atmosphere, sodium hydride (0.115 g, 60% in mineral oil, 2.871 mmol) was added at 0° C. by small portions to a solution of methyl 1-(4-chlorobenzyl)-4-oxopiperidine-3-carboxylate obtained above (0.809 g, 2.871 mmol) in 1.80 mL of anhydrous DMF. The resulting mixture was stirred 30 min at room temperature and then a solution of benzyl bromide (0.341 mL, 2.871 mmol) in 2.20 mL of anhydrous DMF was added. The reaction was followed by HPLC and UPLC-MS. After 24 h at room temperature, it was diluted with ethyl acetate. The organic phase was washed with H2O, brine, dried over Na2SO4 and concentrated in vacuo to give a yellow oil that was purified by flash chromatography (SiO2, petroleum ether:ethyl acetate 95:5 as eluent). Evaporation and drying in vacuo of the pure fractions gave pure methyl 3-benzyl-1-(4-chlorobenzyl)-4-oxopiperidine-3-carboxylate as a colorless oil. (0.623 g, 1.675 mmol, 58% yield). 372.2.

Provenance & Evidence