Potassium Carbonate → 2-(5'-Bromo-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl)ethanol

HRID 1019683Notes

Reaction equation

HRID 1019683 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[NH:9]1[CH2:14][CH2:13][CH:12]([CH:15](O)[CH3:16])[CH2:11][CH2:10]1.C(=O)([O-])[O-:19].[K+].[K+]>CS(C)=O.C(OCC)(=O)C.O>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([N:9]2[CH2:14][CH2:13][CH:12]([CH2:15][CH2:16][OH:19])[CH2:11][CH2:10]2)=[N:3][CH:4]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 693532,5-DibromopyridineHCID 3383211-(Piperidin-4-yl)ethan-1-ol

Product 1

HCID 666607712-(5'-Bromo-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl)ethanol

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
160 °C

Procedure

11.00 g (46.43 mmol) of 2,5-dibromopyridine, 6.00 g (46.43 mmol) of piperidin-4-ylethanol and 6.74 g (48.76 mmol) of potassium carbonate in 8 mL of DMSO are placed in an autoclave. The mixture is then heated at 160° C. for 20 hours. The reaction mixture is allowed to cool to room temperature and then taken up in ethyl acetate and water. The aqueous phase is separated out and extracted twice with ethyl acetate, and the combined organic phases are washed with saturated aqueous sodium chloride solution and dried over sodium sulfate, and the filtrate is concentrated under reduced pressure.

Workup

  1. temperatureto cool to room temperature
  2. customThe aqueous phase is separated out
  3. extractionextracted twice with ethyl acetate
  4. washthe combined organic phases are washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-a7442064e93e473ca91315aacdde63b8
Source dataset
uspto-grants-2014_05
Patent number
US08716289B2

Reaction notes

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