Sodium Hydroxide → N-{4-[1-(2-naphthoyl)-piperidin-4-yl]-butyl}-3-(pyridin-3-yl)-propionamide

Participants

Reaction Conditions

Reaction Steps

6.0 g (20.7 mmol) N-(4-piperidin-4-yl-butyl)-3-(pyridin-3-yl)-propionamide and 2.1 g (20.7 mmol) TEA are dissolved in 30 ml absolute dichloromethane and cooled to ca. 0° C. under moisture exclusion. 3.95 g (20.7 mmol) 2-naphthoyl chloride are dissolved in 40 ml absolute dichloromethane and added dropwise under ice cooling. The mixture is stirred for two hours at RT without further cooling. Subsequently, the batch is made alkaline with 10% sodium hydroxide solution and washed twice with a small amount of water. The organic phase is dried over sodium sulfate and the solvent is removed under vacuum. The resinous residue is chromatographically purified over silica gel with CHCl3/CH3OH (96/4). Yield of colorless resin 5.4 g (59%).

Provenance & Evidence