Oxalyl chloride → 1-(4-Nitrophenyl)piperidine-4-carboxylic acid chloride hydrochloride

Participants

Reaction Conditions

Reaction Steps

To a suspension of 1-(4-nitrophenyl)piperidine-4-carboxylic acid (0.75 g, 3.0 mmol) in dichloromethane (15 mL) is added oxalyl chloride (0.32 mL, 3.6 mmol) and then one drop of N,N-dimethylformamide. The reaction mixture is heated in a 60° C. oil bath under a nitrogen atmosphere for 30 minutes, concentrated under reduced pressure to provide 1-(4-nitrophenyl)piperidine-4-carboxylic acid chloride hydrochloride. N,N-dimethylethylenediamine (1.0 mmol) is added neat to 1-(4-nitrophenyl)piperidine-4-carboxylic acid chloride hydrochloride (0.15 g, 0.5 mmol). The resulting solid is purified by reverse-phase HPLC to provide 1-(4-nitro-phenyl)-piperidine-4-carboxylic acid (2-dimethylamino-ethyl)-amide trifluoroacetate.

Provenance & Evidence