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

HRID 706603Notes

Reaction equation

HRID 706603 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

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 reaction 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 was extracted twice more with ethyl acetate. Concentration of the reaction mixture afforded a viscous oil which was purified on 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).

Workup

  1. customreaction
  2. temperatureheated to 145° C.
  3. stirringstirred in sealed tube for 10 hours
  4. temperatureThe mixture was cooled to ambient temperature
  5. customAfter separation of layers
  6. extractionthe aqueous was extracted twice more with ethyl acetate
  7. customConcentration of the reaction mixture afforded a viscous oil which
  8. customwas purified on a Biotage 40+ Silica column
  9. washeluting with 10% methanol/dichloromethane

Sources & evidence

ORD record
ord-3ac362b8c82a4b4293d950d0e4d73f94
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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