Nitrogen → 7-azido-N-(phenylmethyl)heptanamide

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Reaction Steps

7-azido-N-(phenylmethyl)heptanamide (65) was synthesized from 7-zidoheptanoic acid (64) as shown above. To 120 mg crude 7-azidoheptanoic acid (64) (0.7 mmol, 1.0 eq) was added 1 mL anhydrous THF. To the stirring solution was added 120 mg CDI (0.74 mmol, 1.06 eq) at room temperature. N2 was rapidly evolved from the yellowish slurry. The resulting transparent solution stirred at room temperature for 0.5 h. To the solution was then added 82.5 mg benzylamine (0.77 mmol, 1.1 eq). The solution was stirred 2 h at room temperature followed by solvent removal in vacuo and silica gel chromatography (2:2:1; petroleum ether:Et2O:EtOAc) to render 65 in as a waxy solid (108 mg, 60%). Lyophilization from 50% aqueous CH3CN afforded a fluffy white powder. m.p. slightly above ambient temperature.

Provenance & Evidence