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

HRID 2053670ノート

反応式

HRID 2053670 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-75561f80f2454e58a8349ea640275dc8
出典データセット
uspto-grants-2008_02
特許番号
US07326812B2

反応ノート

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