反应详情

To a 100 ml round-bottomed flask equipped with magnetic stirrer, condenser, and nitrogen inlet were added 0.618 g (2.10 mmol) of N-(1-naphthyl)piperazine 0.472 g (1.95 mmol) of 6-(2-bromoethyl)-benzoxazolone, 0.411 ml (2.92 mmol) of triethylamine, 50 ml ethanol, and a catalytic amount of sodium iodide. The reaction was refluxed for 3 days, cooled, and evaporated to a brown gum. The gum was partitioned between 50 ml water and 75 ml methylene chloride, the pH adjusted with aqueous 1 N sodium hydroxide solution, and a little methanol added to facilitate phase separation. The methylene chloride layer was dried over sodium sulfate and evaporated, then chromatographed on silica gel. Fractions containing the product were combined and evaporated, the residue taken up in ethyl acetate, treated with hydrochloride gas, and the resulting hydrochloride salt of the product filtered off to give the while solid title compound, m.p. 282°-285° C., 213 mg (23% yield).

1. customTo a 100 ml round-bottomed flask equipped with magnetic stirrer, condenser, and nitrogen inlet
2. temperatureThe reaction was refluxed for 3 days
3. temperaturecooled
4. customevaporated to a brown gum
5. customThe gum was partitioned between 50 ml water and 75 ml methylene chloride
6. additiona little methanol added
7. customphase separation
8. dry with materialThe methylene chloride layer was dried over sodium sulfate
9. customevaporated
10. customchromatographed on silica gel
11. additionFractions containing the product
12. customevaporated
13. additiontreated with hydrochloride gas
14. filtrationthe resulting hydrochloride salt of the product filtered off