反应详情

Hydroxylamine hydrochloride (0.5 g, 7.75 mmol) was added to a solution of 4-((2S)-1,4-dibenzylpiperazin-2-yl)benzaldehyde (2.2 g, 5.94 mmol) in 1N aqueous sodium hydroxide (10 ml) and ethanol (10 ml) at room temperature and stirred for 2 hours. The mixture was partitioned between water and chloroform. The organic layer was washed with brine, dried over magnesium sulfate and concentrated in vacuo. The residue was dissolved in acetic acid (10 ml) and was stirred at 80° C. for 6 hours. The solvent was removed under reduced pressure and the residue was partitioned between saturated aqueous sodium bicarbonate and chloroform. The organic layer was washed with brine, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting 5-10% methanol in chloroform to furnish 4-((2S)-1,4-dibenzylpiperazin-2-yl)benzonitrile (1.4 g, 64%) as a colorless oil.

1. customThe mixture was partitioned between water and chloroform
2. washThe organic layer was washed with brine
3. dry with materialdried over magnesium sulfate
4. concentrationconcentrated in vacuo
5. dissolutionThe residue was dissolved in acetic acid (10 ml)
6. stirringwas stirred at 80° C. for 6 hours
7. customThe solvent was removed under reduced pressure
8. customthe residue was partitioned between saturated aqueous sodium bicarbonate and chloroform
9. washThe organic layer was washed with brine
10. dry with materialdried over magnesium sulfate
11. concentrationconcentrated in vacuo
12. customThe residue was purified by silica gel column chromatography
13. washeluting 5-10% methanol in chloroform