Diphenylacetonitrile → HCID 19088487, compound

HRID 1587872Notes

Reaction equation

HRID 1587872 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]([C:27]([CH3:32])([CH2:29][CH2:30]Cl)[CH3:28])[CH3:26])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1(C)C=CC=CC=1>[CH2:18]([N:25]([C:27]([CH3:28])([CH3:32])[CH2:29][CH2:30][C:9]([C:10]#[N:11])([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[CH3:26])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 6837DiphenylacetonitrileHCID 24758Sodium hydrideHCID 19088489HCID 19088489, compound

Product 1

HCID 19088487HCID 19088487, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Sodium hydride (4.4 g of a 60% dispersion in mineral oil) was added in portions to a solution of diphenylacetonitrile (19.3 g) in anhydrous toluene (100 ml). The mixture was heated under reflux for 1.5 hours then allowed to cool to 50° whereupon a solution of 2-(N-benzyl-N-methylamino)-4-chloro-2-methylbutane (11.3 g-see Preparation 11) in anhydrous toluene (20 ml) was added and the mixture heated under reflux for 3 hours. The mixture was partitioned between toluene (200 ml) and 10% aqueous sodium hydroxide (100 ml), the layers separated and the toluene layer washed with water (100 ml). The toluene solution was dried (MgSO4) and concentrated in vacuo to give an oil which was purified by column chromatography on silica eluting with hexane containing toluene (50% up to 100%) and then with toluene containing ethyl acetate (0% up to 10%). The product-containing fractions were combined and concentrated in vacuo to give the title compound as a straw coloured oil, yield 14.5 g.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 1.5 hours
  3. additionwas added
  4. temperaturethe mixture heated
  5. temperatureunder reflux for 3 hours
  6. customThe mixture was partitioned between toluene (200 ml) and 10% aqueous sodium hydroxide (100 ml)
  7. customthe layers separated
  8. washthe toluene layer washed with water (100 ml)
  9. dry with materialThe toluene solution was dried (MgSO4)
  10. concentrationconcentrated in vacuo
  11. customto give an oil which
  12. customwas purified by column chromatography on silica eluting with hexane
  13. additioncontaining toluene (50% up to 100%)
  14. additionwith toluene containing ethyl acetate (0% up to 10%)
  15. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2e4d8e478daa40cc81670d021b091f23
Source dataset
uspto-grants-1993_06
Patent number
US05219871

Reaction notes

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