Phenylacetonitrile → HCID 23084830, compound

HRID 1783305Notes

Reaction equation

HRID 1783305 reaction equation
[C:1]1([CH2:7][C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:10]([O:12][C:13]([N:15]1[CH2:25][CH2:24][CH:18]([C:19](OCC)=[O:20])[CH2:17][CH2:16]1)=[O:14])[CH3:11].[H-].[Na+]>C1(C)C=CC=CC=1>[CH2:10]([O:12][C:13]([N:15]1[CH2:25][CH2:24][CH:18]([C:19]([CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:8]#[N:9])=[O:20])[CH2:17][CH2:16]1)=[O:14])[CH3:11]

Participants

5

Reactant 3

HCID 8794PhenylacetonitrileHCID 24758Sodium hydrideHCID 23084679HCID 23084679, compound

Product 1

HCID 23084830HCID 23084830, compoundYield 61.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

Phenylacetonitrile (5.8 g), ethyl 1-ethoxycarbonylisonipecotate (11.5 g), sodium hydride (purity 60%, 2.0 g) and toluene (25 mL) were mixed, and the mixture was stirred at 80° C. for 3 hrs. After the completion of the reaction, the reaction mixture was cooled to room temperature, and the insoluble material was washed by decantation. The insoluble material was dissolved in water, and acetic acid was added to acidify the mixture, and the mixture was extracted with chloroform. The organic layer was dried over magnesium sulfate, and the solvent was evaporated. The obtained residue was subjected to silica gel column chromatography, and the fraction eluted with hexane:ethyl acetate=2:1 was concentrated to give α-(1-ethoxycarbonylpiperidin-4-yl)carbonylphenylacetonitrile (9.2 g) as an oil.

Workup

  1. customAfter the completion of the reaction
  2. temperaturethe reaction mixture was cooled to room temperature
  3. washthe insoluble material was washed by decantation
  4. dissolutionThe insoluble material was dissolved in water
  5. additionacetic acid was added
  6. extractionthe mixture was extracted with chloroform
  7. dry with materialThe organic layer was dried over magnesium sulfate
  8. customthe solvent was evaporated
  9. washthe fraction eluted with hexane
  10. concentrationethyl acetate=2:1 was concentrated

Sources & evidence

ORD record
ord-1e4fe25b8cb34040a55b9da4c01046c5
Source dataset
uspto-grants-2009_03
Patent number
US07501412B2

Reaction notes

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