Water → HCID 21906225, compound

Participants

Reaction Steps

A solution containing 1-tert-butoxycarbonyl-4-piperidinecarboxaldehyde (500 mg, 2.34 mmol), 2-amino-N-(5-chloropyridin-2-yl)benzamide (580 mg, 0.23 mmol), and pyridinium p-toluenesulfonate (58 mg, 0.23 mmol) in benzene (250 mL) was heated at reflux with azeotropic removal of water. After 16 h, the mixture was concentrated and the residue partitioned between EtOAc (300 mL) and water (150 mL). The organic phase was separated and washed again with water (150 mL), brine (150 mL); then dried with MgSO4, filtered and concentrated to afford, after purification by column chromatography (SiO2: 0 to 10% EtOAc:methylene chloride), 750 mg (72%) of the title compound.

Provenance & Evidence