Potassium Carbonate → 4-(4-Hydroxyazepan-1-yl)benzonitrile

HRID 1468764Notes

Reaction equation

HRID 1468764 reaction equation
Cl.[NH:2]1[CH2:8][CH2:7][CH2:6][CH:5]([OH:9])[CH2:4][CH2:3]1.F[C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[OH:9][CH:5]1[CH2:6][CH2:7][CH2:8][N:2]([C:11]2[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=2)[CH2:3][CH2:4]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 145174-FluorobenzonitrileHCID 53401279Azepan-4-ol--hydrogen chloride (1/1)

Product 1

HCID 679776184-(4-Hydroxyazepan-1-yl)benzonitrileYield 71.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

To a mixture of azepan-4-ol hydrochloride (300 mg, 1.98 mmol) and 4-fluorobenzonitrile (311 mg, 2.57 mmol) in dimethyl sulfoxide (3.00 ml) was added potassium carbonate (821 mg, 5.94 mmol). The mixture was stirred at 120° C. for 6 hours. The mixture was partitioned between water and ethyl acetate. The organic layer was washed with water (three times), dried over sodium sulfate, and concentrated in vacuo. The residue was purified by silica gel column chromatography (eluent; hexane/ethyl acetate=1/4) to afford 4-(4-hydroxyazepan-1-yl)benzonitrile as a yellow solid (306 mg, 1.41 mmol, 71%).

Workup

  1. customThe mixture was partitioned between water and ethyl acetate
  2. washThe organic layer was washed with water (three times)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography (eluent; hexane/ethyl acetate=1/4)

Sources & evidence

ORD record
ord-95fb6b2c13b94d0cb2e392213ee873bd
Source dataset
uspto-grants-2015_04
Patent number
US09006232B2

Reaction notes

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