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-2a2989db33d445c4b96af396a0efd1b0

Source dataset

uspto-grants-2006_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07071358B2