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

HRID 2053670노트

반응식

HRID 2053670 반응식
[F:1][C:2]([F:13])([F:12])[C:3]([C:5]1[CH:10]=[CH:9][C:8](F)=[CH:7][CH:6]=1)=[O:4].C(N(CC)CC)C.[CH:21]1([NH2:26])[CH2:25][CH2:24][CH2:23][CH2:22]1>C(#N)C>[CH:21]1([NH:26][C:8]2[CH:9]=[CH:10][C:5]([C:3](=[O:4])[C:2]([F:13])([F:12])[F:1])=[CH:6][CH:7]=2)[CH2:25][CH2:24][CH2:23][CH2:22]1

참가 물질

5

반응물 3

HCID 2906CyclopentylamineHCID 8471TriethylamineHCID 695642,2,2,4'-Tetrafluoroacetophenone

생성물 1

HCID 220425661-(4-Cyclopentylamino-phenyl)-2,2,2-trifluoro-ethanone

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-75561f80f2454e58a8349ea640275dc8
출처 데이터셋
uspto-grants-2008_02
특허 번호
US07326812B2

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