Morpholine → 2-Fluoro-4-morpholinobenzonitrile

HRID 383960Notes

Reaction equation

HRID 383960 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-973817a883914dbaa25de0e40cd96f96
Source dataset
uspto-grants-2013_02
Patent number
US08367673B2

Reaction notes

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