Morpholine → 2,6-Difluoro-4-(morpholin-4-yl)benzonitrile

HRID 2054890

Reaction equation

HRID 2054890 reaction equation
[F:1][C:2]1[CH:9]=[C:8](F)[CH:7]=[C:6]([F:11])[C:3]=1[C:4]#[N:5].[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.C(N(CC)C(C)C)(C)C>CO.O>[F:1][C:2]1[CH:9]=[C:8]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[CH:7]=[C:6]([F:11])[C:3]=1[C:4]#[N:5]

Participants

6

Reactant 3

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 7371772,4,6-Trifluorobenzonitrile

Product 1

HCID 115286822,6-Difluoro-4-(morpholin-4-yl)benzonitrileYield 68.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 1.0 g (6.37 mmol) of 2,4,6-trifluorobenzonitrile in MeOH (25 mL) was added 0.6 mL (6.9 mmol) of morpholine and 1.2 mL (6.7 mmol) of N,N-diisopropylethylamine. The mixture was heated to 50° C. for 6 h then cooled to room temperature and diluted with H2O which caused a solid to precipitate from solution. The white solid was collected by filtration, washed with H2O and dried under vacuum to provide 0.98 g (68%) of 2,6-difluoro-4-morpholin-4-yl-benzonitrile as a white solid.

Workup

  1. temperaturethen cooled to room temperature
  2. customto precipitate from solution
  3. filtrationThe white solid was collected by filtration
  4. washwashed with H2O
  5. customdried under vacuum

Sources & evidence

ORD record
ord-f2505ceb71034e728e2a4655b9a619a7
Source dataset
uspto-grants-2008_02
Patent number
US07329764B2

Linked notes

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