反应详情

A mixture of N-(6-Aminohexyl)-2-nitrobenzenesulfonamide hydrochloride (0.67 g, 2.0 mmol) and 2-naphthaldehyde(0.32 g, 2.1 mmol) in 75 mL of toluene was refluxed using a Dean Stark trap for 20 h. The reaction mixture was concentrated in vacuo. The residue was dissolved in ethanol (40 mL) and sodium borohyride (0.020 g, 6.0 mmol) was added. After the reaction was complete (6 h), the solvent was evaporated and residue taken up in 30 mL of saturated sodium chloride solution and extracted with ethyl acetate(3×40 mL), washed with saturated sodium chloride solution, dried over sodium sulfate and concetrated to afford an oil. The oil was flash chromatographed over silica gel to afford the titled compound (0.16 g, 37%) which was converted into hydrochloride salt (mp 169° C.).

1. temperaturewas refluxed
2. customfor 20 h
3. concentrationThe reaction mixture was concentrated in vacuo
4. dissolutionThe residue was dissolved in ethanol (40 mL)
5. additionsodium borohyride (0.020 g, 6.0 mmol) was added
6. custom(6 h)
7. customthe solvent was evaporated
8. extractionextracted with ethyl acetate(3×40 mL)
9. washwashed with saturated sodium chloride solution
10. dry with materialdried over sodium sulfate
11. customto afford an oil
12. customchromatographed over silica gel