Morpholine → 4-(6-Nitropyridin-3-yl)morpholine

HRID 272486

反応式

HRID 272486 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1.[NH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.C(=O)([O-])[O-].[K+].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CS(C)=O.C(OCC)(=O)C>[N+:8]([C:5]1[N:6]=[CH:7][C:2]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[CH:3][CH:4]=1)([O-:10])=[O:9]

参加物

7

反応物 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 8176205-Bromo-2-nitropyridine

生成物 1

HCID 29279734-(6-Nitropyridin-3-yl)morpholine収率 54.8%

試薬・触媒・溶媒 3

HCID 67553Tetrabutylammonium Iodide触媒HCID 679Dimethyl Sulfoxide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

5-Bromo-2-nitropyridine (5.14 g, 25.3 mmol), tetra-n-butyl ammonium iodide (0.467 g, 1.27 mmol), morpholine (2.43 g, 27.9 mmol) and potassium carbonate (3.85 g, 27.9 mmol) were mixed in DMSO (50 mL). The reaction mixture was warmed to 80° C. for 15 hours. The reaction mixture was diluted with ethyl acetate and the solids removed by filtration. The organic filtrate was washed with water, then the solvent evaporated. The residue was then triturated with a dichloromethane/hexanes mixture to provide 4-(6-nitro-pyridin-3-yl)-morpholine as brown needles (2.90 g, 54.8%). 1H NMR δ(400 MHz, CDCl3) 8.16 (m, 1H), 7.97 (d, J=2.9 Hz, 1H), 7.15 (dd, J=3.2, 9.3 Hz, 1H), 3.45 (m, 4H), 1.72 (m, 4H).

後処理

  1. customthe solids removed by filtration
  2. washThe organic filtrate was washed with water
  3. customthe solvent evaporated
  4. customThe residue was then triturated with a dichloromethane/hexanes mixture

出典と根拠

ORDレコード
ord-7d5b391c2a7041cd98f9b56ab1f1c162
出典データセット
uspto-grants-2008_11
特許番号
US07456168B2

関連ノート

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