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

Temperature

80 °C

2-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 reaction was added 2-methylpiperazine (5.0 g, 50 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 diethylether (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 evaporated 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 diethylether (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. customevaporated

ORD record

ord-89d057b614224f4394bf1dde4438ae0b

Source dataset

uspto-grants-2006_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07067501B2