Morpholine → 4-(2-Fluoro-4-nitrobenzyl)morpholine

HRID 254932

반응식

HRID 254932 반응식
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH3:11].BrN1C(=O)CCC1=O.[NH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1.C(OCC)(=O)C>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH2:11][N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1

참가 물질

7

반응물 4

HCID 8083MorpholineHCID 8857Ethyl AcetateHCID 67184N-bromobutanimideHCID 740252-Fluoro-4-nitrotoluene

생성물 1

HCID 219550274-(2-Fluoro-4-nitrobenzyl)morpholine수율 55%

시약·촉매·용매 2

HCID 7187Benzoyl Peroxide촉매HCID 5943Carbon Tetrachloride용매

실험 절차

2-Fluoro-4-nitrotoluene (1.55 g, 10 mmol), N-bromosuccinimide (1.82 g, 10 mmol), and benzoyl peroxide (0.1 g, 0.4 mmol) were dissolved in CCl4 (50 mL). The mixture was heated at reflux, and irradiated with light (100 W bulb) for 4 hours. The reaction mixture was then filtered and concentrated. The residue was dissolved in THF (50 mL). Morpholine (1.91 g, 22 mmol) was added to it. The mixture was stirred at ambient temperature for 1 hour and then filtered. The filtrate was evaporated. The bright orange residue was purified by column chromatography eluted with hexane:ethyl acetate, 10:1 to provide 4-(2-fluoro-4-nitrobenzyl)morpholine (1.32 g, 5.5 mmol, yield 55%).

후처리

  1. temperatureThe mixture was heated
  2. temperatureat reflux
  3. customirradiated with light (100 W bulb) for 4 hours
  4. filtrationThe reaction mixture was then filtered
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in THF (50 mL)
  7. filtrationfiltered
  8. customThe filtrate was evaporated
  9. customThe bright orange residue was purified by column chromatography
  10. washeluted with hexane

출처 및 근거

ORD 기록
ord-1f0d58fdd02945cbb88db14fdd94fc01
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07875728B2

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