反应详情

A suspension of 2-chloroquinoline-3-carbaldehyde (93 mg, 0.49 mmol), ethyl trans-{4-[(N-ethylamino)methyl]cyclohexyl}acetate (165 mg, 0.73 mmol) and potassium carbonate (134 mg, 0.97 mmol) in toluene (2 mL) is stirred and refluxed for 3 days. The reaction mixture is cooled to room temperature, diluted with water and ethyl acetate. The organic layer is washed with brine, dried over magnesium sulfate, filtered and concentrated. The crude residue is dissolved with ethanol (1.5 mL) and treated with sodium borohydride (18 mg, 0.48 mmol). The mixture is stirred at room temperature for 2 hours. After addition of sat. ammonium chloride and water, the mixture is extracted with ethyl acetate. The combined organic layer is washed with brine, dried over magnesium sulfate, filtered and concentrated. The crude product is purified by silica gel column chromatography to give ethyl trans-[4-({N-ethyl-N-[3-(hydroxymethyl)quinolin-2-yl]amino}methyl)cyclohexyl]acetate.

1. temperaturerefluxed for 3 days
2. washThe organic layer is washed with brine
3. dry with materialdried over magnesium sulfate
4. filtrationfiltered
5. concentrationconcentrated
6. dissolutionThe crude residue is dissolved with ethanol (1.5 mL)
7. stirringThe mixture is stirred at room temperature for 2 hours
8. extractionthe mixture is extracted with ethyl acetate
9. washThe combined organic layer is washed with brine
10. dry with materialdried over magnesium sulfate
11. filtrationfiltered
12. concentrationconcentrated
13. customThe crude product is purified by silica gel column chromatography