Morpholine → 4-(Pyridin-3-yl)-piperidine-4-carboxylic acid morpholine-amide

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Reaction Steps

Combine 1-benzyl-(4-(pyridin-3-yl)-piperidine-4-carboxylic acid (2.5 g, 8.4 mmol) and morpholine (1.5 g, 16.9 mmol) in dimethylformamide (65 mL). Add 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC) (2.2 g), 1-hydroxy-benzotriazole hydrate (HOBt) (1.6 g), and dimethylformamide (25 mL). After 24 hours, pour the reaction mixture into a saturated aqueous sodium bicarbonate solution and extract twice with diethyl ether. Combine the organic layers, dry over MgSO4, filter, and concentrate to about 50 mL to give solid. Collect the solid by filtration, rinse with diethyl ether, and dry to give 1-benzyl-(4-(pyridin-3-yl)-piperidine-4-carboxylic acid morpholine-amide: Rf =0.67 (silica gel, dichloromethane/methanol/concentrated ammonia 90/10/0.5).

Provenance & Evidence