反应详情

A solution of 3-methoxy-6,7,8,9-tetrahydrobenzocyclohepten-hepten-5-one (6.0 g) and benzylamine (3.4 ml) in toluene (60 ml) in the presence of a catalytic amount of p-toluenesulfonic acid monohydrate was refluxed for 2 hours to remove water at the toluene azeotrope, and then the mixture was evaporated in vacuo. To the residue in methanol (60 ml) was added sodium borohydride (1.2 g) under nitrogen at 5° C., and the mixture was stirred at room temperature for 12 hours. The resulting mixture was poured into ice-cold water and stirred for 30 minutes. After separation, the organic layer was washed with brine, dried over anhydrous magnesium sulfate and evaporated in vacuo. The residue was chromatographed (hexane-ethyl acetate-methanol) over silica gel to afford N-benzyl-(1-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amine (7.27 g).

1. customto remove water at the toluene azeotrope
2. customthe mixture was evaporated in vacuo
3. additionTo the residue in methanol (60 ml) was added sodium borohydride (1.2 g) under nitrogen at 5° C.
4. additionThe resulting mixture was poured into ice-cold water
5. stirringstirred for 30 minutes
6. customAfter separation
7. washthe organic layer was washed with brine
8. dry with materialdried over anhydrous magnesium sulfate
9. customevaporated in vacuo
10. customThe residue was chromatographed (hexane-ethyl acetate-methanol) over silica gel