Cyclopentylamine → 1-(4-Cyclopentylamino-phenyl)-2,2,2-trifluoro-ethanone

To a mixture of 3.94 g of 2,2,2,4′-tetrafluoroacetophenone (20.5 mmol) and 3.35 ml triethylamine (24.0 mmol) in 40 ml of acetonitrile at 0° C. were added 5.9 ml of cyclopentylamine (59.8 mmol). The reaction was allowed to warm to room temperature and then heated to reflux for 14 h. After this time the reaction mixture was cooled to room temperature, concentrated and partitioned between water and EtOAc. The organic layer was dried over MgSO4, filtered and the filtrate was concentrated. The residue was purified by chromatography on silica (hexanes:EtOAc, 4:1) to give the title compound. 1H-NMR (CDCl3) δ 1.53-1.57 (m, 2H), 1.69-1.78 (m, 4H), 2.08-2.13 (m, 2H), 3.88-3.95 (m, 1H), 4.63 (brs, 1H), 6.60 (d, J=8.9 Hz, 2H), 7.92 (d, J=8.9 Hz, 2H). Mass Spectrum (CI+) m/e=258.1 (M+1).

1. temperatureheated
2. temperatureto reflux for 14 h
3. temperatureAfter this time the reaction mixture was cooled to room temperature
4. concentrationconcentrated
5. custompartitioned between water and EtOAc
6. dry with materialThe organic layer was dried over MgSO4
7. filtrationfiltered
8. concentrationthe filtrate was concentrated
9. customThe residue was purified by chromatography on silica (hexanes:EtOAc, 4:1)

ORD record

ord-75561f80f2454e58a8349ea640275dc8

Source dataset

uspto-grants-2008_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07326812B2