Synthesis of N-butyl-4-[(N,N-bis-2'-aminoethyl)amino]-1,8-naphthalimide

CHED 475

Benjamin J. Hale, benhale@uni.edu and Jeffrey E. Elbert, Jeffrey.Elbert@uni.edu. Department of Chemistry and Biochemistry, University of Northern Iowa, MSH 243, Cedar Falls, IA 50614-0423

The synthesis of N-butyl-4-[(N,N-bis-2'-aminoethyl)amino]-1,8-naphthalimide is part of a study of alkyl-1,8-naphthalimide fluorescent probes with cyclic and acyclic polyamine backbones.  The acyclic product is now believed to be even more important due to recent results of the cyclic naphthalimidesBis-(2-aminoethyl)amine is di-protected with di-t-butyl dicarbonate to promote the reaction with the 2'-amine.  The protected triamine is then reacted with N-butyl-1,8-naphthalimide under various conditions.