Methyl p-toluenesulfonate → HCID 22179225, compound

HRID 1795746Notes

Reaction equation

HRID 1795746 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[C:7]#[N:8].[C:9]1([CH3:20])[CH:14]=[CH:13][C:12]([S:15]([O:18]C)(=[O:17])=[O:16])=[CH:11][CH:10]=1>C(#N)C>[C:9]1([CH3:20])[CH:10]=[CH:11][C:12]([S:15]([O-:18])(=[O:16])=[O:17])=[CH:13][CH:14]=1.[C:7]([CH:3]1[CH2:4][CH2:5][CH2:6][N+:2]1([CH3:9])[CH3:1])#[N:8]

Participants

4

Reactant 2

HCID 6645Methyl p-toluenesulfonateHCID 14081616HCID 14081616, compound

Product 1

HCID 22179225HCID 22179225, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In a 250 mL round bottomed flask equipped with a magnetic stir bar, reflux condenser, and pressure-equalizing addition funnel, 10 mmol of 1-methyl-2-pyrrolidinecarbonitrile (16, prepared according to Chiba, et. al., J. Org. Chem. 1977, Vol. 42, No. 18, pp. 2973–7) is dissolved in 50 mL acetonitrile. The mixture is cooled with an ice bath and 10 mmol methyl p-toluenesulfonate (15, available from Aldrich Chemical Company, Inc., Milwaukee, Wis., 53233) is added slowly with stirring under an argon atmosphere. Once the addition is complete, the ice bath is removed and the reaction is warmed to reflux, stirred 16 h, then cooled to room temperature. The solvent is then removed under reduced pressure to obtain 17.

Workup

  1. customIn a 250 mL round bottomed flask equipped with a magnetic stir bar
  2. temperaturereflux condenser, and pressure-equalizing addition funnel
  3. temperatureThe mixture is cooled with an ice bath
  4. additionOnce the addition
  5. customthe ice bath is removed
  6. temperaturethe reaction is warmed
  7. temperatureto reflux
  8. stirringstirred 16 h
  9. customThe solvent is then removed under reduced pressure

Sources & evidence

ORD record
ord-fbe0a29b96b744fb9cc26597a5052eb5
Source dataset
uspto-grants-2006_04
Patent number
US07030075B2

Reaction notes

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