Methanol → HCID 131720621, compound

Participants

Reaction Steps

A mixture of 6-hydroxycinchonine (1) (2.5 g, 8.06 mmol), N-(3-bromopropyl)phthalimide (2.16 g, 8.06 mmol), anhydrous potassium carbonate (1.3 g, 9.4 mmol) and 18-crown-6 (5 mg) in 75 ml of dry acetone was allowed to reflux for 16 h under argon atmosphere. The reaction was cooled to room temperature and 30 ml of methanol was added to make a homogeneous solution. The resulting solution was concentrated and the residue was partially purified on silica gel column chromatography using 5% methanol in chloroform as the eluent. This product was repurified on silica gel column chromatography using 10% methanol in chloroform and yielded 1.08 g (2.17 mmol, 27%) of (11) as off-white solids. MS, IR and NMR data confirmed compound identity.

Provenance & Evidence