反应详情

Combine (1H-benzimidazol-2-yl)-(1-ethoxycarbonyl-piperidin-4-yl)amine (1.5 g, 5.2 mmol) in tetrahydrofuran (45 mL) and dimethylformamide (5 mL). Cool in an ice-bath. Add sodium hydride (0.25 g, 60% n in oil, 6.24 mmol). After 3.5 hours, add 3-(chloromethyl)furan (0.91 g, 7.8 mmol). Warm to ambient temperature. After 60 hours, quench by the addition of Glauber's salt (Na2SO4 10 H2O). Evaporate to remove most of the tetrahydrofuran, dilute with ethyl acetate, and extract with a saturated aqueous sodium bicarbonate solution, water, and then brine. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with ethyl acetate to give (1-(fur-3-ylmethyl)-1H-benzimidazol-2-yl)(1-(ethoxycarbonyl)piperidin-4-yl)amine: Rf=0.32 (silica gel, ethyl acetate).

1. temperatureCool in an ice-bath
2. waitAfter 60 hours
3. customquench by the addition of Glauber's salt (Na2SO4 10 H2O)
4. customEvaporate
5. customto remove most of the tetrahydrofuran
6. additiondilute with ethyl acetate
7. extractionextract with a saturated aqueous sodium bicarbonate solution, water
8. dry with materialDry the organic layer over MgSO4
9. filtrationfilter
10. customevaporate in vacuo
11. customto give a residue