2-Fluoro-5-(trifluoromethyl)benzonitrile → N-(2-Cyano-4-trifluoromethylphenyl)-4-piperidone propylene ketal

HRID 842779Notes

Reaction equation

HRID 842779 reaction equation
F[C:2]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:3]=1[C:4]#[N:5].[CH2:14]1[O:24][C:18]2([CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[O:17][CH:15]1[CH3:16]>C1COCC1.CCOCC.C(=O)([O-])[O-].[Na+].[Na+]>[CH2:14]1[O:24][C:18]2([CH2:23][CH2:22][N:21]([C:2]3[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:3]=3[C:4]#[N:5])[CH2:20][CH2:19]2)[O:17][CH:15]1[CH3:16]

Participants

6

Reactant 2

HCID 5210162-Fluoro-5-(trifluoromethyl)benzonitrileHCID 129541174-Piperidone propylene ketal

Product 1

HCID 86757962N-(2-Cyano-4-trifluoromethylphenyl)-4-piperidone propylene ketal

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 10340Sodium CarbonateSolvent

Procedure

A solution of 2-fluoro-5-trifluoromethylbenzonitrile (2.01 g, 10.61 mmol) and 4-piperidone propylene ketal (1.71 g, 10.9 mmol) in THF (10 mL) was stirred at room temperature (1 h). The resulting mixture was diluted with ether and sodium carbonate solution. The aqueous layer was extracted with two portions of ether and the combined organic extracts were washed with brine, dried over Na2SO4, and concentrated under reduced pressure to afford the title compound (24).

Workup

  1. extractionThe aqueous layer was extracted with two portions of ether
  2. washthe combined organic extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c34c2e854b7b466e9cff29ac461c068a
Source dataset
uspto-grants-2002_04
Patent number
US06376503B1

Reaction notes

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