Dicyclohexylcarbodiimide → Desethyl-N-acetylprocainamide

Participants

Reaction Conditions

Reaction Steps

Desethyl-N-acetylprocainamide was prepared by dissolving 1.0 g of p-acetamidobenzoic acid and 0.7 g N-hydroxysuccinimide in 20 ml pyridine. To this solution was added 1.4 g of N,N'-dicyclohexylcarbodiimide. The reaction mixture was placed at 4° C. for 18 hours, at which time the crystals were removed by filtration. The filtration was brought to room temperature and with stirring, 0.51 g N-ethylethylenediamine was added. Stirring continued for 3 hours, the solution was cooled to 4° C. and allowed to react for an addition 24 hours at 4° C. The second crop of crystals was removed by filtration, dissolved in 25 ml of distilled water. The pH was adjusted to 10 with sodium hydroxide to form a white precipitate of desethyl-N-acetylprocainamide. The resultant precipitate was dried in vacuo and stored at -20° C. in a desiccator.

Provenance & Evidence