Diphenylacetonitrile → HCID 22853757, compound

HRID 21401

Reaction equation

HRID 21401 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[CH2:33][CH2:32][CH2:31][C@@H: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]([C@H:32]1[CH2:31][CH2:30][CH2:29][N:28]([S:18]([C:21]2[CH:22]=[CH:23][C:24]([CH3:25])=[CH:26][CH:27]=2)(=[O:20])=[O:19])[CH2:33]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 538650691-tosyl-3-(R)-(+)-tosyloxypiperidine

Product 1

HCID 22853757HCID 22853757, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Diphenylacetonitrile (13.5 g) was added to a stirred suspension of sodium hydride (3.2 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)-(+)-tosyloxypiperidine (23 g) was added in portions and the mixture heated under reflux for 4 hours. The mixture was diluted with toluene (200 ml) and washed with 10% sodium hydroxide (2×100 ml) and brine (100 ml) then dried (MgSO4) and concentrated in vacuo to give an oil which was purified by column chromatography on silica eluting with toluene containing ethyl acetate (0% up to 10%). The product-containing fractions were combined and concentrated in vacuo to give an oil which was crystallised from ethanol to give the title compound, yield 16 g, m.p. 148°-150° C., [α]D25 -94.4° (c 1.0, CH2Cl2).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. temperaturethe mixture heated
  4. temperatureunder reflux for 4 hours
  5. washwashed with 10% sodium hydroxide (2×100 ml) and brine (100 ml)
  6. dry with materialthen dried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customto give an oil which
  9. customwas purified by column chromatography on silica eluting with toluene
  10. additioncontaining ethyl acetate (0% up to 10%)
  11. concentrationconcentrated in vacuo
  12. customto give an oil which
  13. customwas crystallised from ethanol

Sources & evidence

ORD record
ord-caa7ff901b584c6391dc33d4fdb072d6
Source dataset
uspto-grants-1995_06
Patent number
US05422358

Linked notes

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