4-Fluorobenzonitrile → HCID 178510094, compound

HRID 572242Notes

Reaction equation

HRID 572242 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([OH:8])[CH2:4][CH2:3]1.[H-].[Na+].F[C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=1>CN(C=O)C.CCOC(C)=O>[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([O:8][C:12]2[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=2)[CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 145174-FluorobenzonitrileHCID 24758Sodium hydrideHCID 178511715HCID 178511715, compound

Product 1

HCID 178510094HCID 178510094, compoundYield 44.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of trans-4-aminocyclohexanol (3 g, 26 mmol) in DMF (130 mL) at 0° C. was added 60% sodium hydride in oil. The reaction mixture was stirred at 0° C. for 1 h and then 4-fluorobenzonitrile (3.9 g, 32.6 mmol) was added. It was heated to 60° C. for 2 h and stirred for 12 h at room temperature. The reaction mixture was diluted with EtOAc and washed with water and brine. The organic layer was dried, filtered, and concentrated under reduced pressure to provide the titled compound (2.5 g, 44% yield). 1H NMR (300 MHz, DMSO-d6): δ7.72 (d, J=9 Hz, 2H), 7.09 (d, J=9 Hz, 2H), 4.48-4.34 (m, 1H), 2.68-2.55 (m, 1H), 2.07-1.94 (m, 2H), 1.85-1.71 (m, 2H), 1.46-1.11 (m, 4H).

Workup

  1. temperatureIt was heated to 60° C. for 2 h
  2. stirringstirred for 12 h at room temperature
  3. washwashed with water and brine
  4. customThe organic layer was dried
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c719996c291e44948873a51511342b38
Source dataset
uspto-grants-2015_05
Patent number
US09029401B2

Reaction notes

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