6-Amino-5-chloro-N-{[1-(cyclohexylmethyl)-4-piperidinyl]methyl}-2-(methyloxy)-3-pyridinecarboxamide → 6-Amino-5-chloro-N-{[1-(cyclohexylmethyl)-4-piperidinyl]methyl}-2-oxo-1,2-dihydro-3-pyridinecarboxamide

Participants

Reaction Steps

A solution of 6-amino-5-chloro-N-{[1-(cyclohexylmethyl)-4-piperidinyl]methyl}-2-(methyloxy)-3-pyridinecarboxamide (109 mg, 0.28 mmol) in 10% methanolic hydrogen chloride (8 ml) was refluxed with stirring for 10 h. After cooling to room temperature, the solvent was removed in vacuo. The residue was suspended in methanol/tetrahydrofuran (1:3, 50 ml) and potassium carbonate (ca. 50 mg) was added to the mixture. The mixture was filtered through a pad of Celite and the filtrate was concentrated in vacuo. The residue was chromatographed on a column of aminopropyl silica gel eluting with methanol/dichloromethane (1:3) to give 69 mg (66%) of the title compound as a white solid.

Provenance & Evidence