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

HRID 706661Notes

Reaction equation

HRID 706661 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>O.CCOC(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-amineYield 69.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
145 °C

Procedure

2-Morpholinoethanol (2.21 g, 16.8 mmol) was treated with sodium (0.407 g, 17.7 mmol) until a homogeneous suspension was obtained. 4-Chloropyridin-2-amine (1.14 g, 8.86 mmol) was added and the mixture was heated with magnetic stirring at 145° C. in a sealed tube for 10 hours. The reaction mixture was cooled and diluted with water and EtOAc. The layers were separated, and the aqueous phase was extracted twice with EtOAc. The combined organic extracts were concentrated to afford a viscous oil which was subjected to chromatographic purification on silica with 10% MeOH/DCM as eluent to provide 1.37 g of desired product as a low-melting solid.

Workup

  1. customwas obtained
  2. temperaturethe mixture was heated
  3. temperatureThe reaction mixture was cooled
  4. customThe layers were separated
  5. extractionthe aqueous phase was extracted twice with EtOAc
  6. concentrationThe combined organic extracts were concentrated
  7. customto afford a viscous oil which
  8. customwas subjected to chromatographic purification on silica with 10% MeOH/DCM as eluent

Sources & evidence

ORD record
ord-4971f8f9cc7e41dfbc954fa9da65ab86
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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