Diphenylacetonitrile → {1-[(4-Methylphenyl)sulfonyl]-3-pyrrolidinyl}(diphenyl)acetonitrile

HRID 1742701Notes

Reaction equation

HRID 1742701 reaction equation
[C:1]1([CH:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[S:18]([N:28]1[CH2:32][CH2:31][CH:30](OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:29]1)([C:21]1[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=1)(=[O:20])=[O:19]>C1(C)C=CC=CC=1>[C:8]([C:7]([CH:31]1[CH2:30][CH2:29][N:28]([S:18]([C:21]2[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=2)(=[O:20])=[O:19])[CH2:32]1)([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)#[N:9]

Participants

5

Reactant 3

HCID 6837DiphenylacetonitrileHCID 24758Sodium hydrideHCID 150203551-Tosyl-3-pyrrolidinol Tosylate

Product 1

HCID 22340524{1-[(4-Methylphenyl)sulfonyl]-3-pyrrolidinyl}(diphenyl)acetonitrile

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Diphenylacetonitrile (17.1 g) was added to a stirred suspension of sodium hydride (4 g of a 60% suspension in mineral oil) in anhydrous toluene (250 ml) and the mixture was heated under reflux for 2 hours. On cooling to room temperature, 1-tosyl-3-(R,S)-tosyloxypyrrolidine (28 g--see Preparation 5) was added in portions and the mixture heated under reflux for 3 hours. The mixture was diluted with toluene (150 ml), washed with 5% aqueous sodium hydroxide (2×100 ml) and brine (150 ml) then dried (MgSO4) and concentrated in vacuo to give a solid which was purified by trituration with methanol to give the title compound as a colourless microcrystalline powder, yield 18 g, m.p. 186°-187° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. temperaturethe mixture heated
  4. temperatureunder reflux for 3 hours
  5. washwashed with 5% aqueous sodium hydroxide (2×100 ml) and brine (150 ml)
  6. dry with materialthen dried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customto give a solid which
  9. customwas purified by trituration with methanol

Sources & evidence

ORD record
ord-eef1d824cad74191b0f9b1f7fa7d7fe9
Source dataset
uspto-grants-1994_08
Patent number
US05340831

Reaction notes

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