反应详情

3-(2-benzyloxy-5-bromophenyl)-3-phenylpropyl-p-toluenesulfonate (115 g, 0.2 mole) was dissolved in a mixture of acetonitrile (150 g) and diisopropylamine (202 g, 2.0 mole) and the mixture was refluxed for 4 days. The solution was evaporated, and to the resulting syrup was added sodium hydroxide (2M, 200 mL). The mixture was concentrated, cooled and then extracted with diethyl ether. The ethereal layer was extensively washed with water. The amine was extracted with excess sulfuric acid (1M). The aqueous layer was washed with diethyl ether and then basified with sodium hydroxide (11M). The mixture was then extracted with diethyl ether. The organic layer was washed with water, dried over sodium sulfate, filtered and then evaporated to give 78.6 g (78%) of N,N-diisopropyl-3-(2-benzyloxy-5-bromophenyl)-3-phenylpropylamine as a pale yellow oil. The 1-H N.M.R spectrum was in accordance with the above structure.

1. temperaturethe mixture was refluxed for 4 days
2. customThe solution was evaporated
3. additionto the resulting syrup was added sodium hydroxide (2M, 200 mL)
4. concentrationThe mixture was concentrated
5. temperaturecooled
6. extractionextracted with diethyl ether
7. washThe ethereal layer was extensively washed with water
8. extractionThe amine was extracted with excess sulfuric acid (1M)
9. washThe aqueous layer was washed with diethyl ether
10. extractionThe mixture was then extracted with diethyl ether
11. washThe organic layer was washed with water
12. dry with materialdried over sodium sulfate
13. filtrationfiltered
14. customevaporated