Potassium Hydroxide → 3-(4-Methylpiperazin-1-YL)-5-(trifluoromethyl)aniline

To a mixture of 1-[3-(2,5-dimethyl-1H-pyrrol-1-yl)-5-(trifluoromethyl)phenyl]-4-methylpiperazine (440 mg, 1.3 mmol) and potassium hydroxide (1.46 g, 26. mmol) in EtOH (10 mL) and water (3 mL) was added hydroxylamine hydrochloride (2.72 g, 39 mmol. The reaction mixture was heated at reflux overnight. The reaction mixture was then concentrated and the residue was dissolved in water and EtOAc. The reaction mixture was extracted with EtOAc. The organic solutions were combined, washed with brine, dried over Na2SO4 filtered and concentrated. The residue was purified by column chromatography to give 3-(4-methylpiperazin-1-yl)-5-(trifluoromethyl)aniline (247 mg, 73%) as a yellow oil. 1H NMR (300 MHz, CDCl3) δ: 6.55 (d, 1H), 6.40 (d, 1H), 6.33 (d, 1H), 3.24 (t, 4H), 2.61 (t, 4H), and 2.38 (s, 3H). LCMS: (FA) ES+ 260.2.

1. temperatureThe reaction mixture was heated
2. temperatureat reflux overnight
3. concentrationThe reaction mixture was then concentrated
4. dissolutionthe residue was dissolved in water
5. extractionThe reaction mixture was extracted with EtOAc
6. washwashed with brine
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. concentrationconcentrated
10. customThe residue was purified by column chromatography

ORD-Eintrag

ord-f3493cec472e415b869a1c544c5eb413

Quelldatensatz

uspto-grants-2012_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08110687B2