alpha-Naphthyl isocyanate → N-{4-[1-(Naphthylaminocarbonyl)-piperidin-4-yl]-butyl}-3-(pyridin-3-yl)-propionamide

Participants

Reaction Steps

2.6 g (17.7 mmol) 1-naphthyl isocyanate are dissolved in 15 ml abs. THF and cooled to 0° C. under moisture exclusion. 5.1 g (17.7 mmol) N-(4-piperidine-4-yl-butyl)-3-(pyridine-3-yl)-propionamide are dissolved in 35 ml abs. THF and added dropwise under ice cooling. The mixture is stirred without further cooling at RT overnight. Subsequently, the solution is drawn off under vacuum to a large extent and the residue is chromatographically purified over silica gel with CHCl3/CH3OH (90/10) and further purified by flash-chromatography with CHCl3/CH3OH (95/5 to 90/10). After drawing off the solvent, crystallization occurs from isopropanol/diisopropanol. Colorless crystals with a MP of 143-144° C. were recovered; yield 0.77 g (9%).

Provenance & Evidence