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

HRID 254932

反応式

HRID 254932 の反応式
[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

参加物

7

反応物 4

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

生成物 1

HCID 219550274-(2-Fluoro-4-nitrobenzyl)morpholine収率 55%

試薬・触媒・溶媒 2

HCID 7187Benzoyl Peroxide触媒HCID 5943Carbon Tetrachloride溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-1f0d58fdd02945cbb88db14fdd94fc01
出典データセット
uspto-grants-2011_01
特許番号
US07875728B2

関連ノート

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