Diisopropylcarbodiimide → 4-(4-Iodo-phenyl)-1-methyl-piperidine-4-carboxylic acid (3,5-dichloro-phenyl)-amide

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Reaction Steps

To a solution of 4-(4-iodo-phenyl)-1-methyl-piperidine-4-carboxylic acid pyridine salt (440 mg, 1.04 mmol, see Example 6) and 3,5-dichlorophenylaniline (0.20 g, 1.24 mmol, 1.2 eq.) in anhydrous DMF (5 mL) was added DIC (0.326 mL, 2.08 mmol, 2 eq.) followed by DMAP (0.006 g, 0.052 mmol, 5 mol %). The mixture was stirred at room temperature for 16 h and then it was partitioned between EtOAc (50 mL) and saturated aqueous NaHCO3 (50 mL). The organic layer was separated, washed with H2O (3×40 mL) and saturated brine (50 mL), dried over Na2SO4, filtered and concentrated by rotary evaporation. The crude material was purified by silica gel chromatography by eluting with 10% MeOH/EtOAc to give 175 mg (34%) of 4-(4-iodo-phenyl)-1-methyl-piperidine-4-carboxylic acid (3,5-dichloro-phenyl)-amide as a white solid. MS(ESI): 489.1/491.1.

Provenance & Evidence