2-(Dimethylamino)ethanol → HCID 22607746, compound

HRID 2307750Notes

Reaction equation

HRID 2307750 reaction equation
[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][OH:5].[H-].[Na+].[Br:9][C:10]1[CH:11]=[N:12][CH:13]=[C:14](Br)[CH:15]=1>CN(C=O)C>[Br:9][C:10]1[CH:15]=[C:14]([O:5][CH2:4][CH2:3][N:2]([CH3:6])[CH3:1])[CH:13]=[N:12][CH:11]=1

Participants

5

Reactant 3

HCID 79022-(Dimethylamino)ethanolHCID 24758Sodium hydrideHCID 693693,5-Dibromopyridine

Product 1

HCID 22607746HCID 22607746, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N,N-dimethylethanolamine(0.5 mL) in DMF (10 mL) at room temperature was treated with sodium hydride (0.2 g, 8.4 mmol), stirred for 30 minutes, and treated with 3,5-dibromopyridine (1.0 g, 4.2 mmol). The mixture was stirred at 90° C. for 8 hours, and partitioned between ethyl acetate and water. The organic layer was washed with brine, dried (Na2SO4), filtered, and concentrated under vacuum. Purification by flash column chromatography on silica gel with 50% ethyl acetate/hexane provided the desired product (0.8 g, 78%). MS (DCI/NH3) m/e 246 (M+H)+.

Workup

  1. stirringThe mixture was stirred at 90° C. for 8 hours
  2. custompartitioned between ethyl acetate and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customPurification by flash column chromatography on silica gel with 50% ethyl acetate/hexane

Sources & evidence

ORD record
ord-0fd6b9c448cc47ccb39d7a543ca9fd21
Source dataset
uspto-grants-2004_12
Patent number
US06831175B2

Reaction notes

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