2-Fluoro-5-methylbenzonitrile → N-(2-Cyano-4-methylphenyl)-4-piperidone propylene ketal

HRID 842782Notes

Reaction equation

HRID 842782 reaction equation
F[C:2]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:3]=1[C:4]#[N:5].[CH2:11]1[O:21][C:15]2([CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)[O:14][CH:12]1[CH3:13]>CN(C=O)C.CCOCC.C(=O)([O-])[O-].[Na+].[Na+]>[CH2:11]1[O:21][C:15]2([CH2:20][CH2:19][N:18]([C:2]3[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:3]=3[C:4]#[N:5])[CH2:17][CH2:16]2)[O:14][CH:12]1[CH3:13]

Participants

6

Reactant 2

HCID 27745842-Fluoro-5-methylbenzonitrileHCID 129541174-Piperidone propylene ketal

Product 1

HCID 86757963N-(2-Cyano-4-methylphenyl)-4-piperidone propylene ketal

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 10340Sodium CarbonateSolvent

Procedure

A solution of 2-fluoro-5-methylbenzonitrile (2.76 g, 20.4 mmol) and 4-piperidone propylene ketal (3.39 g, 21.5 mmol) in DMF (50 mL) was heated in an oil bath (90° C., 20 h). The mixture was diluted with ether and sodium carbonate solution. The aqueous layer was extracted with two additional portions of ether and the combined organic extracts were washed with brine, dried over Na2SO4, and concentrated under reduced pressure. PCTLC (SiO2, 6 mm, 50-0% hexane/CHCl3) afforded the title compound (29).

Workup

  1. extractionThe aqueous layer was extracted with two additional 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-2ca31ef732be4aaaa27a5267183f06eb
Source dataset
uspto-grants-2002_04
Patent number
US06376503B1

Reaction notes

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