反应详情

3,5-Bis(trifluoromethyl)benzylamine (0.305 g, 1.25 mmol) was added to a solution of 2-(4-cyclohexylmethyl-piperazin-1-yl)-quinoline-3-carbaldehyde (0.4 g, 1.23 mmol) in methanol followed by acetic acid (0.15 mL) at ambient temperature under nitrogen atmosphere. After stirring 1 h, sodium cyanoborohydride (0.237 g, 3.77 mmol) was added carefully, and the reaction was stirred at RT for overnight. The reaction mixture was evaporated to dryness, and water (30 mL) and ethyl acetate (30 mL) were added to the residue, and this was then extracted with ethyl acetate (2×30 mL). The combined organic phases were washed with brine, dried over sodium sulfate, filtered, and concentrated under vacuum to afford a pale yellow crude product. Purification by silica gel column chromatography and eluting with 2.5% methanol/dichloromethane afforded the title compound (0.468 g), yield: 67%.

1. stirringthe reaction was stirred at RT for overnight
2. customThe reaction mixture was evaporated to dryness, and water (30 mL) and ethyl acetate (30 mL)
3. additionwere added to the residue
4. extractionthis was then extracted with ethyl acetate (2×30 mL)
5. washThe combined organic phases were washed with brine
6. dry with materialdried over sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated under vacuum
9. customto afford a pale yellow crude product
10. customPurification by silica gel column chromatography
11. washeluting with 2.5% methanol/dichloromethane