Morpholine → 4-(5-bromopyridin-2-yl)morpholine

HRID 1021267Notes

Reaction equation

HRID 1021267 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](Cl)=[N:6][CH:7]=1.[NH:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1>CN(C)C(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 27344145-Bromo-2-chloropyridine

Product 1

HCID 109667244-(5-bromopyridin-2-yl)morpholine

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
130 °C

Procedure

5-Bromo-2-chloropyridine (5.0 g) was mixed with N,N-dimethylacetamide (25 ml), and morpholine (23 ml) was added thereto, followed by stirring at 130° C. for 2 days. The reaction mixture was concentrated under reduced pressure, and water was added to the residue, followed by extraction with EtOAc, and the organic layer was washed with saturated brine and dried over Na2SO4. The organic layer was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/EtOAc) to obtain 4-(5-bromopyridin-2-yl)morpholine (6.07 g).

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated under reduced pressure, and water
  3. additionwas added to the residue
  4. extractionfollowed by extraction with EtOAc
  5. washthe organic layer was washed with saturated brine
  6. dry with materialdried over Na2SO4
  7. concentrationThe organic layer was concentrated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-bafc666d8c6c4fd09f3405f2b9654f78
Source dataset
uspto-grants-2014_05
Patent number
US08716470B2

Reaction notes

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