Piperidine → N-(4-Amino-2-benzyloxy-phenyl)-2-benzyloxy-nicotinamide

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Reaction Steps

{3-Benzyloxy-4-[(2-benzyloxy-pyridine-3-carbonyl)-amino]-phenyl}-carbamic acid 9H-fluoren-9-ylmethyl ester (424) (0.430 g, 0.664 mmol) was dissolved in a mixture of THF (6 mL) and DMF (3 mL). Piperidine (12.88 mmol) was added. The mixture was shaken at room temperature for 1 h. LC-MS indicated complete de-protection at this point. The mixture was concentrated under reduced pressure to give a dark brown/purple oil. Purification by flash chromatography on silica gel using a gradient of hexane and EtOAc (15–100% EtOAc/hexane 25 minutes) gave the desired product (425) as an orange oil upon concentration (0.229 g, 0.538 mmol, 81% yield). LC-MS (ESI): (exact mass: 425.17) m/e=426.2 [M+1]+ (100%).

Provenance & Evidence