Editing Synthesis Lipophilic Polyamines (section)

=== C: Tetraethylenepentamine (TEPA)<br><br>  ===

The unreduced intermediate for this compound was synthesized by dissolving 190 mL (1 mmol) TEPA in 6 mL of dioxane with 349 mL (2 mmol) of N,N-diiso-propylethylamine and then adding 662 mL (2 mmol) of oleoyl chloride. The reaction mixture was stirred 16 h at 56 ° C and dioxane was evaporated under vacuum. The residue was dissolved in chloroform and applied to a silica gel column. The column was washed with chloroform, the product was eluted by chloroform/methanol (96:4) and the solvent was evaporated. The yield was 150 mg ('''21%'''). R f was 0.8 on TLC on Silica Gel 60 F254 in chloroform/methanol (3:0.5). Proton NMR (in CDCl 3 ): d 0.85 (6H), 1.28 (44H), 1.6 (4H), 1.75 (3H), 2.00 (8H), 2.25 (4H), 2.50 (8H), 3.4 (4H), 5.35 (4H) and 6.50 (2H). The intermediate was reduced with LiAlH 4 as described for the synthesis of compound A. The yield was 99 mg ('''88%'''). R f was 0.55 on TLC on Cellulose Polygram  Cell 300 (Brinkmann Instruments, Westbury, NY, USA) in ethanol/water/HCl (100:60:2). Proton NMR (in CDCl 3 ): d 0.88 (6H), 1.25 (48H), 2.00 (8H), 2.55 (20H) and 5.35 (4H). 

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