Reaktion #40876

Reaktionsgleichung

1-[4-(trifluoromethyl)phenyl]butan-1-one

hydroxylamine hydrochloride

→

title compound

Ausbeute 83.0%

(R/S)-1-[4-(trifluoromethyl)phenyl]butan-1-amine

Ausbeute 83.0%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe reaction heated
2. 2
   Temperaturto reflux
3. 3
   Einengenconcentrated in vacuo
4. 4
   Waschenwashed twice with water
5. 5
   Trocknendried over sodium sulfate
6. 6
   Einengenconcentrated in vacuo
7. 7
   workup.DISSOLUTIONThe crude oxime was then dissolved in ethanol (100 ml)
8. 8
   workup.ADDITIONRaney nickel (approx 1 g) added
9. 9
   workup.STIRRINGThe reaction was stirred under a balloon of hydrogen for 72 h
10. 10
    FiltrationThe reaction was filtered though celite (washing with ethanol)
11. 11
    Einengenconcentrated in vacuo
12. 12
    Sonstigepurified by flash column (50-80% ethyl acetate in hexanes)

Vorschrift

To a solution of 1-[4-(trifluoromethyl)phenyl]butan-1-one (6 g, 27.8 mmol) in ethanol (60 ml) was added hydroxylamine hydrochloride (5.79 g, 83.3 mmol) and the reaction heated to reflux and stirred for 16 h. The reaction was allowed to cool to room temperature and then concentrated in vacuo. The residue was taken up in ethyl acetate, washed twice with water, dried over sodium sulfate and concentrated in vacuo. The crude oxime was then dissolved in ethanol (100 ml) and Raney nickel (approx 1 g) added. The reaction was stirred under a balloon of hydrogen for 72 h. The reaction was filtered though celite (washing with ethanol) concentrated in vacuo, adsorbed onto silica gel and purified by flash column (50-80% ethyl acetate in hexanes) to yield the title compound (5 g, 83%) as colourless crystals.

Quelle