Syntheses of tertiary tetraamines and quaternary pentaamines with three and four methylene chain units

Article abstract of DOI:10.1248/cpb.40.2958

Tertiary tetraamines and quaternary pentaamines composed of aminopropyl and/or aminobutyl groups were synthesized as authentic samples for the identification of naturally occurring branched polyamines. Four tertiary tetraamines were obtained by alkylating the free secondary amine group of diphthaloyl derivatives of sym-norspermidine or sym-homospermidine with N-(3-bromopropyl)phthalimide or N-(4-bromobutyl)phthalimide in the presence of KF-Celite. Five quaternary pentaamines were obtained by fusing triphthaloyl derivatives of the tertiary tetraamines with an excess amount of N-(3-iodopropyl)phthalimide or N-(4-iodobutyl)phthalimide. The present methods are simple and achieved high yields. The ¹³C-NMR spectra of these branched polyamines were recorded in D₂O as fully protonated forms, and all ¹³C chemical shifts were assigned consistently.

Full text of DOI:10.1248/cpb.40.2958

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