4-Pyridinecarboxylic acid, 1-oxide → HCID 86745660, compound

Participants

Reaction Steps

To a mixture of 4.50 g (15.5 mmol) of 4-(5,6,7,12-tetrahydrobenzocycloocta[1,2-b]pyridin-12-ylidene) piperidine, 2.19 g (15.7 mmol) of isonicotinic acid N-oxide, and 2.33 g (17.2 mmol) of 1-hydroxybenzotriazole hydrate in 30 mL of dry methylene chloride at -15° C. and under a nitrogen atmosphere was added dropwise over 25 min. a solution of 3.26 g (16.9 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride in 60 mL of dry methylene chloride. The reaction mixture was slowly allowed to warm to room temperature. After 3 hours the mixture was poured into a solution of 10% aqueous sodium dihydrogen phosphate and extracted with methylene chloride (3x). The combined organic portions were dried over MgSO4, filtered, and concentrated in vacuo to give a product which was purified via flash chromatography to give 1-(4-pyridinyl carbonyl)-4-(5,6,7,12-tetrahydrobenzocycloocta[1,2-b]pyridin-12-ylidene)piperidine N-oxide as a colorless glass.

Provenance & Evidence