Editing Synthesis Lipophilic Polyamines (section)

=== A: N,N′-Bis(3-aminopropyl)ethylenediamine<br>  ===

<br>Add 662 mL of oleoyl chloride to 184 mL of N,N′-Bis(3-aminopropyl)ethylenediamine &nbsp; in 8 mL of dioxane. <br> 

Stir the mixture&nbsp; for 16 h at 70 °C.<br> 

Evaporate the dioxane under vacuum<br> 

Dissolve the residue&nbsp; in 2 mL of chloroform. <br> 

Purify on silica gel column-chromatography (eluent:chloroform/methanol 98:2) <br> 

Yield: 180 mg (15.4% yield) of the unreduced intermediate. <br> 

R f is 0.85 on thin-layer chromatography (TLC) on Silica Gel 60 F254 (Alltech Associates, Deerfield, IL, USA) in chloroform/methanol (3:0.6). Proton nuclear magnetic resonance (NMR) (in CDCl 3 ): d 0.87 (12H), 1.25 (88H), 1.7 (4H), 2.00 (16H), 2.2 (8H), 3.4 (12H), 5.35 (8H) and 6.65 (2H). <br> 

Dissolve the intermediate in tetrahydrofurane (THF)<br> 

Add slowly&nbsp; to a stirring suspension of LiAlH4,<br> 

Stir the reaction mixture for 72 h at 55 °C.<br>Add ethyl acetate (1 mL) and 1 N NaOH (0.8 mL) <br> 

Filter.<br> 

Wash the precipitate two times with THF. <br> 

Dry the the filtrate and washings of the precipitate&nbsp; (with MgSO 4 ) and evaporate.<br> 

Purify by silica gel column-chromatography (eluent: CHCl3&nbsp;: CH3OH 96:4)<br> 

Yield is 7.6%. <br> 

R f was 0.7 on TLC on Silica Gel 60 F254 in chloroform/methanol (3:0.5). <br> 

Proton NMR (in CDCl 3 ): d 0.87 (12H), 1.25 (96H), 1.87 (2H), 2.00 (16H), 2.50 (4H), 2.8 (20H) and 5.38 (8H). 

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