Diphenylacetonitrile → HCID 19970193, compound

HRID 974966Notes

Reaction equation

HRID 974966 reaction equation
[H-].[Na+].[C:3]1([CH:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:10]#[N:11])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:18]([N:25]1[CH2:30][CH2:29][CH:28]([CH2:31]Cl)[CH2:27][CH2:26]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1(C)C=CC=CC=1>[CH2:18]([N:25]1[CH2:30][CH2:29][CH:28]([CH2:31][C:9]([C:10]#[N:11])([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:27][CH2:26]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 6837DiphenylacetonitrileHCID 24758Sodium hydrideHCID 4309591-Benzyl-4-(chloromethyl)piperidine

Product 1

HCID 19970193HCID 19970193, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Sodium hydride (1.69 g, 42.1 mmol; 80% dispersion in oil) was added portionwise over 10 minutes to a solution of diphenylacetonitrile (7.4 g, 38.3 mmol) in toluene (40 ml) and the mixture was heated under reflux for 45 minutes, treated with 1-benzyl-4-chloromethylpiperidine (4.3 g, 1.92 mmol; prepared by partitioning the hydrochloride salt, which was obtained by the method described in J. Het. Chem., 1978, 15, 675, between 10% aqueous sodium carbonate solution and dichloromethane, drying the organic layer over magnesium sulphate and evaporating), heated under reflux for one hour, allowed to cool to room temperature and partitioned between toluene and water. The organic layer was dried over magnesium sulphate and evaporated. The residue was purified by chromatography on silica using dichloromethane plus 0-5% methanol as eluant. Appropriate fractions were combined and evaporated to give the title compound (7.57 g, 52%) as a colourless foam which was characterised by its 1H-NMR spectrum.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 45 minutes
  3. customprepared
  4. customby partitioning the hydrochloride salt
  5. customwhich was obtained by the method
  6. dry with material, 1978, 15, 675, between 10% aqueous sodium carbonate solution and dichloromethane, drying the organic layer over magnesium sulphate
  7. customevaporating),
  8. temperatureheated
  9. temperatureunder reflux for one hour
  10. custompartitioned between toluene and water
  11. dry with materialThe organic layer was dried over magnesium sulphate
  12. customevaporated
  13. customThe residue was purified by chromatography on silica
  14. customevaporated

Sources & evidence

ORD record
ord-5c9f7cf20f8f447d8dfaf5dbab062990
Source dataset
uspto-grants-1997_03
Patent number
US05607950

Reaction notes

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