Morpholine → 4-Phenylmorpholine

HRID 641900

反応式

HRID 641900 の反応式
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1.N1CCC[C@H]1C(O)=O>[Cu]I.CS(C)=O>[C:2]1([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 8083MorpholineHCID 11575IodobenzeneHCID 145742L-Proline

生成物 1

HCID 623394-Phenylmorpholine収率 44.4%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
90 °C

実験手順

1-iodobenzene (28.12 g, 137.84 mmol) was added to morpholine (12.0 g, 137.93 mmol). L-Proline (3.12 g, 27.13 mmol) was then added, followed by the addition of CuI (2.6 g, 13.68 mmol) and DMSO (120 mL). The resulting solution was stirred at 90° C. for 4 hours, and then the reaction mixture was then quenched by the addition of 300 mL of iced water. The resulting solution was extracted using dichloromethane (2×200 mL), and the organic layers combined, dried (Na2SO4) and concentrated. The residue was purified by column chromatography using a petroleum ether solvent system. The collected fractions were combined and concentrated to give 10 g (42%) of 4-phenylmorpholine as a white solid.

後処理

  1. customthe reaction mixture was then quenched by the addition of 300 mL of iced water
  2. extractionThe resulting solution was extracted
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-4164fd1b61e74a6d9f80aaaaffc40ee9
出典データセット
uspto-grants-2010_04
特許番号
US07696229B2

関連ノート

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