Reaktion #941205

Reaktionsgleichung

THF

6-acetylamino-1-tetralone

N,N-dimethylmethylene ammonium chloride

→

compound

6-Acetylamino-2-(N,N-dimethylamino)methyltetralin

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenconcentrated
2. 2
   workup.ADDITIONAn aqueous solution of 10% potassium carbonate was added to the residue, which
3. 3
   Extraktionwas then extracted with ethyl acetate
4. 4
   WaschenThe organic layer was washed with a saturated aqueous sodium chloride solution
5. 5
   Sonstigedried
6. 6
   Einengenconcentrated
7. 7
   workup.DISSOLUTIONThe residue was dissolved in methanol (50 ml), to which
8. 8
   workup.ADDITIONwas added sodium borohydride (0.86 g)
9. 9
   workup.STIRRINGThe reaction mixture was stirred at room temperature for 1 hour
10. 10
    workup.ADDITIONwater was added
11. 11
    Extraktionwhich was then extracted with ethyl acetate
12. 12
    WaschenThe organic layer was washed with a saturated aqueous sodium chloride solution
13. 13
    Sonstigedried
14. 14
    Einengenconcentrated
15. 15
    workup.DISSOLUTIONThe residue was dissolved in methanol (50 ml), to which
16. 16
    workup.ADDITIONwere added 10% palladium-carbon (0.4 g) and 1 N hydrochloric acid (20 ml)
17. 17
    workup.WAITfor 12 hours
18. 18
    SonstigeThe palladium-carbon was removed from the reaction mixture through filtration
19. 19
    Einengenthe filtrate was concentrated
20. 20
    workup.ADDITIONan aqueous solution of 10% potassium carbonate was added
21. 21
    Sonstigeto form a free form compound
22. 22
    ExtraktionThen, this was extracted with ethyl acetate
23. 23
    WaschenThe organic layer was washed with a saturated aqueous sodium chloride solution
24. 24
    Sonstigedried
25. 25
    Einengenconcentrated
26. 26
    SonstigeThe resulting crude crystals were recrystallized from ethyl acetate-hexane

Vorschrift

A THF solution (40 ml) of 6-acetylamino-1-tetralone (1.692 g) was added to an acetonitrile solution (40 ml) of N,N-dimethylmethylene ammonium chloride (2.04 g), then stirred at room temperature for 24 hours, and concentrated. An aqueous solution of 10% potassium carbonate was added to the residue, which was then extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, then dried, and concentrated. The residue was dissolved in methanol (50 ml), to which was added sodium borohydride (0.86 g). The reaction mixture was stirred at room temperature for 1 hour, and water was added thereto, which was then extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, then dried, and concentrated. The residue was dissolved in methanol (50 ml), to which were added 10% palladium-carbon (0.4 g) and 1 N hydrochloric acid (20 ml). Then, this was catalytically reduced under a hydrogen pressure of 1 atmosphere, for 12 hours. The palladium-carbon was removed from the reaction mixture through filtration, the filtrate was concentrated, and an aqueous solution of 10% potassium carbonate was added thereto to form a free form compound. Then, this was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, then dried, and concentrated. The resulting crude crystals were recrystallized from ethyl acetate-hexane to obtain the entitled compound (1.862 g).

Quelle