Water → HCID 60754209, compound

HRID 1961430Notes

Reaction equation

HRID 1961430 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[NH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]1[CH2:16][OH:17].C([O-])(O)=O.[Na+].O>CN(C=O)C>[OH:17][CH2:16][CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][N:10]1[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 145174-FluorobenzonitrileHCID 94263Piperidin-2-ylmethanolHCID 516892Sodium Bicarbonate

Product 1

HCID 60754209HCID 60754209, compoundYield 9.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

In a screw cap pressure tube, 4-fluorobenzonitrile (354.0 mg, 3.15 mmol), piperidin-2-ylmethanol (363.4 mg, 3.15 mmol) and NaHCO3 were suspended in DMF (2.0 ml). The tube was sealed and the mixture heated to 120° C. for 3 days. The mixture was allowed to cool. H2O was added and the product extracted with EtOAc. The combined organic extracts were washed with H2O, dried (MgSO4), filtered and concentrated. The crude product was purified by flash chromatography (CH2Cl2/MeOH 98:2→96:4) affording 63 mg (9%) of the title compound.

Workup

  1. customIn a screw cap pressure tube
  2. customThe tube was sealed
  3. temperatureto cool
  4. extractionthe product extracted with EtOAc
  5. washThe combined organic extracts were washed with H2O
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was purified by flash chromatography (CH2Cl2/MeOH 98:2→96:4)

Sources & evidence

ORD record
ord-03719eddbb164e53bdaff68e47905e8c
Source dataset
uspto-grants-2013_04
Patent number
US08415333B2

Reaction notes

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