Morpholine → 2-Fluoro-4-morpholinobenzonitrile

HRID 45608Notes

Reaction equation

HRID 45608 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-fe7c453dc1e84ed48bb0650f1f54c9d5
Source dataset
uspto-grants-2013_09
Patent number
US08541579B2

Reaction notes

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