Reaktion #60388

Reaktionsgleichung

6-(2-dimethylamino-ethoxy)-3,4-dihydro-2H-naphthalen-1-one oxime

HCl

→

compound

6-(2-dimethylamino-ethoxy)-1,2,3,4-tetrahydro-naphthalen-1-ylamine

Lösungsmittel

EtOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas purged with H2
2. 2
   Sonstigeconnected to a H2 balloon overnight at RT
3. 3
   FiltrationThe catalyst was filtered through Celite®
4. 4
   Waschenwashed with MeOH
5. 5
   EinengenThe filtrate was concentrated in vacuo
6. 6
   workup.ADDITIONThe residue was added saturated NaHCO3
7. 7
   Extraktionextracted with CH2Cl2
8. 8
   TrocknenThe organic solution was dried over Na2SO4
9. 9
   Filtrationfiltered
10. 10
    Einengenconcentrated in vacuo
11. 11
    SonstigeThe crude product was purified by silica gel chromatography (5%-10% MeOH—CH2Cl2)

Vorschrift

A mixture of 6-(2-dimethylamino-ethoxy)-3,4-dihydro-2H-naphthalen-1-one oxime (0.3 g, 1.2 mmol), EtOH (12 mL), Pd/C (Aldrich, 0.13g, 0.12 mmol), and concentrated HCl (0.24 mL) was purged with H2 and connected to a H2 balloon overnight at RT. The catalyst was filtered through Celite® and washed with MeOH. The filtrate was concentrated in vacuo. The residue was added saturated NaHCO3 and extracted with CH2Cl2. The organic solution was dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by silica gel chromatography (5%-10% MeOH—CH2Cl2) to afford the compound as a colorless oil. MS (ESI): 235 (M+H)+.

Quelle