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The mechanism of the conversion of secondary amines by sodium hypochlorite (NaOCl) to compounds that form fluorescent adducts with ο-phthalaldehyde (OPA)/2-mercaptoethanol (ME) was investigated by analyzing the reaction mixtures of secondary amines and NaOCl by high performance liquid chromatography (HPLC) and high performance thin-layer chromatography (HPTLC). Methylamine was found to be produced from N-methylamino acids, L-epinephrine, DL-metanephrine and N-methylcyclohexylamine. While N-phenylbenzylamine and N-alkylbenzylamines gave aniline and the corresponding alkylamines, respectively, N-alkylanilines produced the corresponding alkylamines rather than aniline. α-Amino acids were converted to ammonia by NaOCl. On the basis of these findings, mechanism of the conversion of secondary amines to primary amines by NaOCl were proposed.

Mechanism of conversion of secondary amines to primary amines by sodium hypochlorite.