Triethylamine → 2-(3-Methylpiperazin-1-YL)aniline

Temperature

80 °C

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%)

1. temperatureto cool to room temperature before the solvent
2. extractionthe product was extracted with diethyether (2×200 mL)
3. extractionextracted with ethyl acetate (2×200 mL)
4. washwashed with saturated brine
5. dry with materialdried over magnesium sulfate
6. filtrationfiltered
7. concentrationthe filtrate was concentrated in vacuo
8. dissolutionThe product (10.5 g) was dissolved in ethanol (250 mL)
9. additionPalladium on charcoal catalyst (10% w/w, 2.2 g) was added to the solution
10. filtrationThe solution was filtered
11. customthe solvents evaporated in vacuo

ORD record

ord-86d131ef29ac455bb0d330f31ba0e749

Source dataset

uspto-grants-2012_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08110567B2