反应详情

N-(3-Nitrophenylacetyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-methylisoquinoline (22.0 g, 0.059 m) was added portionwise to 190 ml of 1 M borane in THF which was maintained under a nitrogen atmosphere. The mixture was stirred at ambient temperature for 15 minutes, then heated to reflux for 4 hours. The mixture was cooled in an ice bath, treated carefully with 20% HCl (250 ml), and then refluxed for 1 hour. After cooling, the solvents were removed on an aspirator and the residue treated with 250 ml 20% NaOH and extracted with chloroform (3×200 ml). The extracts were dried over MgSO6 and evaporated to an oily residue. The residue was dissolved in methanol (100 ml) and treated with HCl gas until acidic. Upon cooling, a yellow solid was obtained which was collected by filtration and dried to give 23.2 g N-(3-nitrophenethyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-methylisoquinoline hydrochloride, m.p. 139°-140°.

1. temperaturewas maintained under a nitrogen atmosphere
2. temperatureheated
3. temperatureto reflux for 4 hours
4. temperatureThe mixture was cooled in an ice bath
5. temperaturerefluxed for 1 hour
6. temperatureAfter cooling
7. customthe solvents were removed on an aspirator
8. additionthe residue treated with 250 ml 20% NaOH
9. extractionextracted with chloroform (3×200 ml)
10. dry with materialThe extracts were dried over MgSO6
11. customevaporated to an oily residue
12. dissolutionThe residue was dissolved in methanol (100 ml)
13. additiontreated with HCl gas until acidic
14. temperatureUpon cooling
15. customa yellow solid was obtained which
16. filtrationwas collected by filtration
17. customdried