反应详情

1-(4-Hydroxyphenyl)cyclohexanecarbonitrile (1.70 g, 8.45 mmol), 1-(3-chloro-propyl)-pyrrolidine (1.87 g, 12.67 mmol), acetone (50 mL), sodium iodide (0.444 g, 2.96 mmol) and K2CO3 (5.45 g, 39.44 mmol) were heated to 50° C. overnight. The solvent was evaporated and the crude product was taken into DCM, washed with 0.5N NaOH, extracted with 0.5N HCl solution and washed with DCM. The aqueous layer was basified with 0.5N NaOH and extracted with DCM. The combined organic extracts were dried over Na2SO4, filtered, washed with DCM and concentrated in vacuo to give a yellowish solid. The solid was slurried in ether, filtered, washed with ether to give the title compound as a white solid (1.34 g, 51%). 1H NMR (400 MHz, CDCl3) δ7.30 (d, 2H), 6.83 (d, 2H), 3.95 (t, 2H), 2.54 (t, 2H), 2.44 (m, 4H), 2.06 (m, 2H), 1.92 (m, 2H), 1.84-1.58 (m, 12H).

1. customThe solvent was evaporated
2. washwashed with 0.5N NaOH
3. extractionextracted with 0.5N HCl solution
4. washwashed with DCM
5. extractionextracted with DCM
6. dry with materialThe combined organic extracts were dried over Na2SO4
7. filtrationfiltered
8. washwashed with DCM
9. concentrationconcentrated in vacuo
10. customto give a yellowish solid
11. filtrationfiltered
12. washwashed with ether