Reaktion #1726676

Reaktionsgleichung

Fluoronitrobenzene

triethylamine

Ethyl acetate

2-methyl-piperazine

→

aniline

2-(3-Methylpiperazin-1-yl)phenylamine

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto cool to room temperature before the solvent
2. 2
   Extraktionthe product was extracted with diethyether (2×200 mL)
3. 3
   Extraktionextracted with ethyl acetate (2×200 mL)
4. 4
   Waschenwashed with saturated brine
5. 5
   Trocknendried over magnesium sulfate
6. 6
   Filtrationfiltered
7. 7
   Einengenthe filtrate was concentrated in vacuo
8. 8
   workup.DISSOLUTIONThe product (10.5 g) was dissolved in ethanol (250 mL)
9. 9
   workup.ADDITIONPalladium on charcoal catalyst (10% w/w, 2.2 g) was added to the solution
10. 10
    FiltrationThe solution was filtered
11. 11
    Sonstigethe solvents evaporated in vacuo

Vorschrift

Fluoronitrobenzene (7.1 g, 50 mmol) was dissolved in DMF (100 mL) containing triethylamine (10 g, 100 mmol) and placed under a nitrogen atmosphere. To the solution was added 2-methyl-piperazine (5.5 g, 55 mmol). The reaction was heated to 80° C. for 16 hours. The reaction was allowed to cool to room temperature before the solvent was reduced to half volume in vacuo. Ethyl acetate (200 mL) and ice-water (250 mL) were added to the solution and the product was extracted with diethyether (2×200 mL). The aqueous phase was saturated with sodium chloride and extracted with ethyl acetate (2×200 mL). The organic phases were combined, washed with saturated brine, dried over magnesium sulfate, filtered and the filtrate was concentrated in vacuo. The product (10.5 g) was dissolved in ethanol (250 mL). Palladium on charcoal catalyst (10% w/w, 2.2 g) was added to the solution and the solution was hydrogenated in a Parr apparatus at 3 bar for 3 hours. The solution was filtered and the solvents evaporated in vacuo to give the aniline product. Yield (8.0 g, 83%)

Quelle