Fragmentation During the Formic Acid/Formaldehyde (Eschweiler-Clarke) Methylation of Polyamines

Article abstract of DOI:10.1016/0040-4039(91)80583-R

Eschweiler-Clarke methylations of both acyclic and cyclic polyamines can lead to methylation products of fragments of the original polyamine; thus 1,5,9,13-tetra-azatridecane yields 1,1,3,3-tetramethylpropanediamine exclusively and 1,5,9-triazacyclododecane gives 45 percent 1,5,9-trimethyl-1,5,9-triazacyclododecane and 45 percent 2,6,10-trimethyl-2,6,10-triazaundecane.