反应详情

N-(4-Nitrophenylacetyl)-1,2,3,4-tetrahydro-6,7-dimethoxyisoquinoline (28.45 g, 0.08 m) was added portionwise to a stirred solution of 1 M borane in tetrahydrofuran (320 ml, 0.32 m) which was diluted with 180 ml of dry tetrahydrofuran and maintained under nitrogen. The mixture was heated to reflux for 3 hours, then cooled in an ice bath and carefully treated with 100 ml of 20% HCl. The mixture was heated to reflux for 1 hour, then allowed to cool. The solvent was removed at an aspirator (40°) and the residue slurried with cold water (400 ml) and the solid collected by filtration, washed with water and air dried. The hydrochloride salt was prepared in 300 ml of a methanol, isopropanol, ether mixture and dried to give 18.0 g N-(4-nitrophenethyl)-1,2,3,4-tetrahydro-6,7-dimethoxyisoquinoline hydrochloride, m.p. 154°-155°.

1. temperaturemaintained under nitrogen
2. temperatureThe mixture was heated
3. temperatureto reflux for 3 hours
4. temperaturecooled in an ice bath
5. temperatureThe mixture was heated
6. temperatureto reflux for 1 hour
7. temperatureto cool
8. customThe solvent was removed at an aspirator (40°)
9. filtrationthe residue slurried with cold water (400 ml) and the solid collected by filtration
10. washwashed with water and air
11. customdried
12. dry with materialisopropanol, ether mixture and dried