Water → [1-(Pyrimidin-2-yl)piperidin-4-yl]methanol

HRID 1485108Notes

Reaction equation

HRID 1485108 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][OH:8])[CH2:3][CH2:2]1.Cl[C:10]1[N:15]=[CH:14][CH:13]=[CH:12][N:11]=1.C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O.C(OCC)(=O)C>[N:11]1[CH:12]=[CH:13][CH:14]=[N:15][C:10]=1[N:1]1[CH2:6][CH2:5][CH:4]([CH2:7][OH:8])[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 744042-ChloropyrimidineHCID 4207714-Piperidinemethanol

Product 1

HCID 2776521[1-(Pyrimidin-2-yl)piperidin-4-yl]methanolYield 89.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4-piperidinemethanol (1.00 g) in dimethyl sulfoxide (28.9 mL), 2-chloropyrimidine (994 mg) and potassium carbonate (2.40 g) were added and the mixture was stirred at 100° C. for three hours. After cooling the reaction mixture to room temperature, water was added to it and extraction was conducted with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and after removing the desiccant by filtration, the filtrate was concentrated under reduced pressure to give [1-([pyrimidin-2-yl)piperidin-4-yl]methanol as a colorless oil (1.50 g).

Workup

  1. temperatureAfter cooling the reaction mixture to room temperature
  2. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  3. customafter removing the
  4. filtrationdesiccant by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a1999d9a8d8c4eabbe8845792a9825cc
Source dataset
uspto-grants-2016_08
Patent number
US09422240B2

Reaction notes

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