反应详情

A mixture of 1-[1-(4-chlorophenyl)cyclobutyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (7.29 g prepared as described in Example 50), allyl bromide (2.66 g), anhydrous potassium carbonate (5.52 g) and acetone (100 ml) was heated under reflux for 2 hours. The reaction mixture was filtered and the solvent was removed by evaporation to give a residue which was digested with a 9:1 mixture of petroleum ether and triethylamine. The solution was decanted from a residual tar, filtered and the solvent removed to give a residue. A sample of this residue (3 g) was heated under reflux in a nitrogen atmosphere with glacial acetic acid (50 ml) and 48% hydrobromic acid (50 ml) for 7 hours. The reaction mixture was added to ice/water and excess aqueous ammonia solution added slowly under nitrogen. The resulting mixture was extracted with ethyl acetate. The organic layer was evaporated and the residue dissolved in ethyl acetate. Addition of a solution of oxalic acid in ethyl acetate gave 2-allyl-1-[1-(4 -chlorophenyl)cyclobutyl]-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline oxalate [m.p. 85° C. (dec)] which was dried in air.

1. temperaturewas heated
2. temperatureunder reflux for 2 hours
3. filtrationThe reaction mixture was filtered
4. customthe solvent was removed by evaporation
5. customto give a residue which
6. customThe solution was decanted from a residual tar
7. filtrationfiltered
8. customthe solvent removed
9. customto give a residue
10. additionadded slowly under nitrogen
11. extractionThe resulting mixture was extracted with ethyl acetate
12. customThe organic layer was evaporated
13. dissolutionthe residue dissolved in ethyl acetate
14. additionAddition of a solution of oxalic acid in ethyl acetate