反应详情

温度

60 °C

To a solution of 300 mg (0.92 mmol) 2-methyl-4-[2-(4-trifluoromethyl-phenyl)-ethyl]-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine in 13 mL acetonitrile was added 210.3 mg (0.92 mmol) 2-Bromo-N-methyl-2-phenyl-acetamide (commercially available), 473 uL (2.76 mmol) N-ethyldiisopropylamine and 138 mg (0.92 mmol) sodium iodide. The solution was stirred for 18 h at 60° C. The solvent was removed in vacuo and the residue was dissolved in ethyl acetate and washed with water and Na2CO3 aq. The organic layer was dried over Na2SO4, filtered and evaporated. The residue was purified on silica eluting with a gradient formed from heptane and ethyl acetate. The diastereoisomeric product eluting first (obtained after evaporation from the product containing fractions) was dissolved in methanol, treated with Norit, heated to reflux, filtered and evaporated to dryness to yield 46 mg (11%) of N-methyl-2-{2-methyl-4-[2-(4-trifluoromethyl-phenyl)-ethyl]-6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl}-2-phenyl-acetamide (diastereoisomer 1) (MS(m/e): 472.9 (MH+)) as light yellow oil.

1. customThe solvent was removed in vacuo
2. dissolutionthe residue was dissolved in ethyl acetate
3. washwashed with water and Na2CO3 aq. The organic layer
4. dry with materialwas dried over Na2SO4
5. filtrationfiltered
6. customevaporated
7. customThe residue was purified on silica eluting with a gradient
8. customformed from heptane and ethyl acetate
9. washThe diastereoisomeric product eluting first (
10. customobtained
11. customafter evaporation from the product
12. additioncontaining fractions)
13. dissolutionwas dissolved in methanol
14. additiontreated with Norit
15. temperatureheated
16. temperatureto reflux
17. filtrationfiltered
18. customevaporated to dryness