2-Morpholinoethanol → 4-(2-Morpholinoethoxy)pyridin-2-amine

HRID 79300

反応式

HRID 79300 の反応式
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][OH:9])[CH2:3][CH2:2]1.[Na].Cl[C:12]1[CH:17]=[CH:16][N:15]=[C:14]([NH2:18])[CH:13]=1>C(OCC)(=O)C.O>[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][O:9][C:12]2[CH:17]=[CH:16][N:15]=[C:14]([NH2:18])[CH:13]=2)[CH2:3][CH2:2]1

参加物

6

反応物 3

HCID 611632-MorpholinoethanolHCID 5818662-Amino-4-chloropyridineHCID 5360545Sodium

生成物 1

HCID 672520854-(2-Morpholinoethoxy)pyridin-2-amine

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

2-Morpholinoethanol (2.2 g, 16.8 mmol) was treated with sodium (116 mg, 5.0 mmol) in a sealed tube and stirred at ambient temperature until homogeneous. 4-Chloropyridin-2-amine (1.1 g, 8.9 mmol) was added and the reaction mixture was heated to 145° C. and stirred in sealed tube for 10 hours. The mixture was cooled to ambient temperature before diluting with ethyl acetate and water. After separation of layers, the aqueous phase was extracted twice more with ethyl acetate. Concentration under vacuum afforded a viscous oil which required purification using a Biotage 40+Silica column eluting with 10% methanol/dichloromethane to give 4-(2-morpholinoethoxy)pyridin-2-amine as a viscous oil which solidified upon further drying under high vacuum (1.4 g).

後処理

  1. temperaturethe reaction mixture was heated to 145° C.
  2. stirringstirred in sealed tube for 10 hours
  3. temperatureThe mixture was cooled to ambient temperature
  4. customAfter separation of layers
  5. extractionthe aqueous phase was extracted twice more with ethyl acetate
  6. concentrationConcentration under vacuum
  7. customafforded a viscous oil which required
  8. custompurification
  9. washeluting with 10% methanol/dichloromethane

出典と根拠

ORDレコード
ord-7881bf40dd23452485bd5402d187fa18
出典データセット
uspto-grants-2014_09
特許番号
US08841455B2

関連ノート

読み込み中…