反应详情

A solution of 2-(4-bromophenyl)-N-{2-(3-methoxyphenyl)ethyl}-N-phenylacetamide (1.0 g, 2.4 mmol) in phosphorous oxychloride (10 mL) under nitrogen was heated to 80° C. After 15 hours, the reaction was cooled to RT and slowly poured over ice. Potassium iodide (0.78 g, 4.7 mmol) was then added to the mixture, and after 30 minutes, the quinolinium salt was extracted with ethyl acetate (2×100 mL). The organic layer was dried over MgSO4, filtered and concentrated. The residue was then dissolved in methanol (25 mL), and sodium borohydride (0.27 g, 7.2 mmol) was slowly added. After 30 minutes, the reaction was concentrated and partitioned between ethyl acetate and water. The organic layer was dried over MgSO4, filtered and concentrated to provide the title compound (0.20 g, 21% yield): 1H NMR (CDCl3) 6.6-7.4 (m, 12H), 4.82 (t, 1H), 3.60 (s, 3H), 3.58 (m, 2H), 2.6-3.2 (m 4H); EI-MS (m/z) 407.

1. additionslowly poured over ice
2. waitafter 30 minutes
3. extractionthe quinolinium salt was extracted with ethyl acetate (2×100 mL)
4. dry with materialThe organic layer was dried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated
7. dissolutionThe residue was then dissolved in methanol (25 mL)
8. waitAfter 30 minutes
9. concentrationthe reaction was concentrated
10. custompartitioned between ethyl acetate and water
11. dry with materialThe organic layer was dried over MgSO4
12. filtrationfiltered
13. concentrationconcentrated