Synthesis of N1,N1,N3,N3-tetrasubstituted diethylenetriamines

Abstract

Preparative procedures for the synthesis of N¹,N¹,N³,N³-tetrasubstituted diethylenetriamines via aminoalkylation of N,N-disubstituted ethylenediamines with N,N-disubstituted 2-chloroethylamines were developed. Aminoalkylation of N,N-dimethylethylenediamine under heating gave simultaneously secondary N¹,N¹,N³,N³-tetrasubstituted diethylenetriamines and quaternary ammonium salts, N-(2-aminoethyl)-N-(2-dialkylaminoethyl)-N,N-dimethylammonium chlorides. Structures of the synthesized compounds were established by IR spectroscopy, ¹H and ¹³C NMR spectroscopy, and electrospray ionization mass spectrometry.