Diphenylacetonitrile → HCID 19970192, compound

HRID 974978Notes

Reaction equation

HRID 974978 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.[CH3:18][C:19]1[CH:24]=[CH:23][C:22]([S:25]([N:28]2[CH2:33][CH2:32][CH:31]([CH2:34]OS(C3C=CC(C)=CC=3)(=O)=O)[CH2:30][CH2:29]2)(=[O:27])=[O:26])=[CH:21][CH:20]=1>C1(C)C=CC=CC=1.O>[C:10]([C:9]([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)[CH2:34][CH:31]1[CH2:30][CH2:29][N:28]([S:25]([C:22]2[CH:21]=[CH:20][C:19]([CH3:18])=[CH:24][CH:23]=2)(=[O:26])=[O:27])[CH2:33][CH2:32]1)#[N:11]

Participants

6

Reactant 3

HCID 6837DiphenylacetonitrileHCID 24758Sodium hydrideHCID 19970200HCID 19970200, compound

Product 1

HCID 19970192HCID 19970192, compoundYield 86.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

Sodium hydride (3.2 g, 80 mmol; 60% dispersion in oil) was added to a stirred solution of diphenylacetonitrile (13.5 g, 70 mmol) in toluene (200 ml) and the mixture was heated under reflux for 2 hours, treated with a solution of 1-(4-methylphenylsulphonyl)-4-(4-methylphenylsulphonyloxymethyl)piperidine (25.0 g, 60 mmol--see Preparation 15) in toluene (50 ml), heated under reflux for a further 2 hours, allowed to cool to room temperature and diluted with water. The layers were separated and the organic layer was washed with water and saturated brine, dried over magnesium sulphate and evaporated. The residue was crystallised from ethanol to give the title compound (23.0 g, 86%) as colourless crystals, m.p. 130° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. temperatureheated
  4. temperatureunder reflux for a further 2 hours
  5. customThe layers were separated
  6. washthe organic layer was washed with water and saturated brine
  7. dry with materialdried over magnesium sulphate
  8. customevaporated
  9. customThe residue was crystallised from ethanol

Sources & evidence

ORD record
ord-4ff72583b4cf4bf882d339ff73a4c3a0
Source dataset
uspto-grants-1997_03
Patent number
US05607950

Reaction notes

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