Morpholine → (3-Chloro-4-morpholinopyridin-2-yl)methanol

HRID 1655208Notes

Reaction equation

HRID 1655208 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Cl:7][C:8]1[C:9]([CH2:15][OH:16])=[N:10][CH:11]=[CH:12][C:13]=1Cl>C(O)C>[O:4]1[CH2:5][CH2:6][N:1]([C:13]2[CH:12]=[CH:11][N:10]=[C:9]([CH2:15][OH:16])[C:8]=2[Cl:7])[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 221173013,4-Dichloro-2-(hydroxymethyl)pyridine

Product 1

HCID 19791250(3-Chloro-4-morpholinopyridin-2-yl)methanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Morpholine (7.34 ml) and 3.4 -dichloro-2 -hydroxymethylpyridine (3.0 g) were heated together in a bomb at 180 ° for 4 hours. After cooling, the mixture was taken up in ethanol and evaporated under reduced pressure to remove excess amine. The residue was taken up in water and extracted with chloroform. After drying (K2CO3 ) and removal of solvent, the residue was chromatographed (silica gel, CHCl3) to give an oil which was crystallised from petroleum ether (60/80 ) to give 4 -morpholino-3 -chloro-2 -hydroxymethylpyridine, 3.24 g, m.p. 80°-2°.

Workup

  1. temperatureAfter cooling
  2. customevaporated under reduced pressure
  3. customto remove excess amine
  4. extractionextracted with chloroform
  5. customAfter drying
  6. custom(K2CO3 ) and removal of solvent
  7. customthe residue was chromatographed (silica gel, CHCl3)
  8. customto give an oil which
  9. customwas crystallised from petroleum ether (60/80 )

Sources & evidence

ORD record
ord-731ba16b5b2e4e72a148519e2fcef5de
Source dataset
uspto-grants-1993_10
Patent number
US05250527

Reaction notes

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