Selective benzoylation of primary amines in the presence of secondary amines

Article abstract of DOI:10.1016/S0040-4039(99)01396-9

Compounds containing both primary and secondary amine moieties in the same molecule were treated sequentially with two equivalents of n-butyllithium at room temperature, two equivalents of TMSCI, one equivalent of n-butyllithium and one equivalent of benzoyl chloride, to afford mono-benzoylated diamines. Under these conditions, the primary amine moiety was selectively benzoylated.