Sodium hydride → HCID 11149549, compound

HRID 1627556Notes

Reaction equation

HRID 1627556 reaction equation
[H-].[Na+].[NH:3]1[CH2:8][CH2:7][CH:6]([OH:9])[CH2:5][CH2:4]1.Br[C:11]1[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][N:12]=1>CS(C)=O>[Br:17][C:14]1[CH:15]=[CH:16][C:11]([O:9][CH:6]2[CH2:7][CH2:8][NH:3][CH2:4][CH2:5]2)=[N:12][CH:13]=1

Participants

5

Reactant 3

HCID 24758Sodium hydride2×HCID 693532,5-DibromopyridineHCID 79341Piperidin-4-ol

Product 1

HCID 11149549HCID 11149549, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Sodium hydride (56 mg, 2.3 mmol) was added to a solution of piperidin-4-ol (214 mg, 2.11 mmol) in DMSO (8 mL). After stirring for 30 minutes, 2,5-dibromopyridine was added. After stirring for 24 hours, sodium hydride (56 mg, 2.3 mmol) was added. After stirring for another 24 hours the reaction was partitioned between ethyl acetate and water. The phases were separated and the aqueous phase was extracted with ethyl acetate. The combined organic phases were dried over MgSO4 and concentrated by rotary evaporation. The residue was purified by silica gel chromatography using gradient elution of dichloromethane, methanol, ammonium hydroxide to afford 5-bromo-2-(piperidin-4-yloxy)-pyridine (316 mg, 58%).

Workup

  1. stirringAfter stirring for 24 hours
  2. stirringAfter stirring for another 24 hours the reaction
  3. customwas partitioned between ethyl acetate and water
  4. customThe phases were separated
  5. extractionthe aqueous phase was extracted with ethyl acetate
  6. dry with materialThe combined organic phases were dried over MgSO4
  7. concentrationconcentrated by rotary evaporation
  8. customThe residue was purified by silica gel chromatography
  9. washelution of dichloromethane, methanol, ammonium hydroxide

Sources & evidence

ORD record
ord-f5b7b399bd8941f299303e317472bca3
Source dataset
uspto-grants-2014_07
Patent number
US08785632B2

Reaction notes

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