Bis(2-hydroxybenzyl)-4-(p-nitrobenzyl)diethylenetriamine → Bis(2-hydroxybenzyl)-4-(p-aminobenzyl)diethylenetriamine

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Reaction Steps

In 40 mL of absolute ethanol was dissolved 400 mg of bis(2-hydroxybenzyl)-4-(p-nitrobenzyl)diethylenetriamine (prepared in Example 1) and 100 mg of palladium on activated charcoal (10% Pd). The mixture was hydrogenated at 40 psi (275.8 kPa) for 24 hours. The catalyst was removed by filtration. The ethanolic solution was evaporated to provide bis(2-hydroxybenzyl)-4-(p-aminobenzyl)diethylenetriamine, and was characterized by: 1H NMR (CDCl3), carbon protons only; amine and hydroxyl protons were not included: δ 2.6 (s, 8H), 3.4 (s, 2H), 3.8 (s, 4H), 6.4-7.2 (m, 12H). 13C NMR (CDCl3) δ 46.06, 52.35, 53.48, 58.74, 115.08, 116.33, 118.87, 122.50, 128.35, 128.62, 130.03, 145.74, 158.31.

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