8-Aminoquinoline → 1-Acetyl-N-(quinolin-8-yl)-4-piperidinecarboxamide

Participants

Reaction Conditions

Reaction Steps

A solution of 8-aminoquinoline (48.50 g) in dimethylformamide (300 ml) was stirred at 80° C., under nitrogen, as a mixture of 1-acetylpiperidine-4-carbonyl chloride hydrochloride (106.30 g) and potassium carbonate (93.0 g) was added in portions. The slurry was stirred at 80° C. overnight, quenched with water (1200 ml) and extracted with dichloromethane. The extracts were dried over anhydrous magnesium sulfate, filtered, and the filtrate was evaporated. The residue was purified first by high performance liquid chromatography (silica; 25:1 dichloromethane-methanol), followed by flash chromatography (silica; 50:1 dichloromethane-methanol). The appropriate fractions were collected and evaporated to give 58.5 g (58.6%) of product, as an oil.

Provenance & Evidence