Morpholine → 2-Fluoro-4-morpholinobenzonitrile

HRID 2108694Notes

Reaction equation

HRID 2108694 reaction equation
[F:1][C:2]1[CH:9]=[C:8](F)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[NH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1>O1CCCC1>[F:1][C:2]1[CH:9]=[C:8]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

4

Reactant 2

HCID 8083MorpholineHCID 775452,4-Difluorobenzonitrile

Product 1

HCID 210699252-Fluoro-4-morpholinobenzonitrileYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2,4-difluorobenzonitrile (6.03 g, 43.35 mmol) and morpholine (8.3 ml, 95.17 mmol) in tetrahydrofuran (27 ml) was stirred at room temperature for 24 hr. The mixture was evaporated and the white solid purified by Biotage™ column (90 g, silica) eluting with cyclohexane:ethyl acetate: (4:1) to give 2-fluoro-4-(morpholino)-benzonitrile as a white solid (5.81 g, 65%).

Workup

  1. customThe mixture was evaporated
  2. customthe white solid purified by Biotage™ column (90 g, silica)
  3. washeluting with cyclohexane

Sources & evidence

ORD record
ord-cb427f90ad764b84a77e8920999eed22
Source dataset
uspto-grants-2009_04
Patent number
US07514437B2

Reaction notes

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