Acetic Acid → HCID 19884960, compound

Participants

Reaction Steps

A 250 ml three-neck round bottom flask was charged with 2.2 g (7.6 mmol) of 1-phenyl-3-(4-methyl-1-naphthalenyloxy)propanamine and 100 ml of acetonitrile. To the mixture was added a 37% formaldehyde solution (3.02 ml, 37.8 mmol). The mixture was stirred for approximately 20 minutes while moderate heat was applied to maintain the reaction mixture as a solution. Next, 760 mg (12.1 mmol) of sodium cyanoborohydride was added to the reaction mixture, and the mixture was stirred for five hours at room temperature. The pH of the reaction mixture was maintained at approximately 6.5 by the addition of glacial acetic acid. The reaction mixture was acidified and stirred for 30 minutes. The mixture was concentrated under vacuum and made basic by the addition of 5N sodium hydroxide. Ten drops of triethylamine were added. The mixture was extracted three times with diethyl ether, and the organic extracts were combined and washed with water and a saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The organic phase was concentrated under vacuum to provide 2.6 g of an oil. The oil was purified by high pressure liquid chromatography employing a methanol/methylene chloride gradient as the eluent. The free base was converted to the oxalate salt and recrystallized from ethyl acetate to provide 1.5 g of the title compound. mp=110°-112.5° C.

Provenance & Evidence