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

HRID 586517

反応式

HRID 586517 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-37fe36c73def478fa5119c4c399ed3e8
出典データセット
uspto-grants-2005_08
特許番号
US06936612B2

関連ノート

読み込み中…