Methanol → HCID 86749665, compound

Participants

Reaction Steps

A solution of 7-{3-[(7-methoxy-chroman-2-ylmethyl-amino]-propanoxy}-quinoline (2.19 g, 5.7 mmol) in 48% aqueous HBr was heated to reflux for 3 hours. The reaction mixture was then allowed to cool to room temperature and basified with 1N sodium hydroxide until pH 12. The basic reaction mixture was extracted with ethyl acetate (2×100 mL), dried over anhydrous magnesium sulfate, filtered, and the solvent removed under vacuum. Chromatography (7% methanol in methylene chloride containing 1% ammonium hydroxide) afforded 1.34 g of the title compound (63% yield). The corresponding oxalate salt was prepared by adding an excess of oxalic acid in warm ethanol to a solution of the free base in warm ethanol; mp 195.5°-196.5° C.

Provenance & Evidence