反应详情

温度

60 °C

3-Methoxyphenylethylamine (1.5 g) and benzaldehyde (1.0 mL) were reacted together in benzene (10 mL) in a modified Dean-Stark apparatus, where the side arm contained activated 3 Å molecular sieve beads. The reaction was vigorously refluxed for 1 h until a uniform solution resulted. The reaction was cooled and evaporated. The resulting residue was taken up in trifluoroacetic acid (6 mL) and heated to 60° C. for 18 h. The reaction was cooled, concentrated then partitioned between 1N sodium hydroxide (70 mL) and diethyl ether (50 mL). The organic layer was washed with 0.5 N sodium hydroxide (70 mL), dried, concentrated to 20 mL and cooled in an ice-water bath. The crystals that formed were collected and dried to give the title compound (1.90 g). MS: 240.0 (MH+); HPLC tR: 1.62 min (method D); 1H NMR (DMSO-d6+TFA-d): 7.47-7.49 (m, 3H), 7.37-7.39 (m, 2H), 6.90 (broad s, 1H), 6.79 (dd, 1H, J=2.4, 8.7 Hz), 6.66 (d, 1H, J=8.7 Hz), 5.75 (s, 1H), 3.77 (s, 3H), 3.39-3.44 (m, 2H), 3.17-3.28 (m, 1H), 3.04-3.12 (m, 1H).

1. temperatureThe reaction was vigorously refluxed for 1 h until a uniform solution
2. customresulted
3. temperatureThe reaction was cooled
4. customevaporated
5. temperatureThe reaction was cooled
6. concentrationconcentrated
7. customthen partitioned between 1N sodium hydroxide (70 mL) and diethyl ether (50 mL)
8. washThe organic layer was washed with 0.5 N sodium hydroxide (70 mL)
9. customdried
10. concentrationconcentrated to 20 mL
11. temperaturecooled in an ice-water bath
12. customThe crystals that formed
13. customwere collected
14. customdried