Chlorosuccinimide → 1-(5-bromo-2-chlorophenyl)-N-(cyanomethyl)piperidine-2-carboxamide

Participants

Reaction Conditions

Reaction Steps

To a suspension of 1-(3-bromophenyl)-N-(cyanomethyl)-2-piperidinecarboxamide (2.25 g, 6.98 mmol, prepared as described in example 25) in 70 mL of isopropyl alcohol was added N-chlorosuccinimide (1.02 g, 7.68 mmol). The suspension was heated to 60° C. and the resultant solution was stirred at 60° C. for 2 h. The mixture was cooled and partitioned between ethyl acetate and brine. The aqueous layer was extracted with ethyl acetate (3 ×) and the combined organic layers were dried over Na2SO4 and concentrated. Purification by flash chromatography (50% Et2O/hexanes) yielded 1-(5-bromo-2-chlorophenyl)-N-(cyanomethyl)piperidine-2-carboxamide (faster eluting compound) and 1-(3-bromo-4-chlorophenyl)-N-(cyanomethyl)piperidine-2-carboxamide (slower eluting compound).

Provenance & Evidence