p-Toluenesulfonic acid → 1-Pyrrolidino-1-cyclohexene

HRID 1635909Notes

Reaction equation

HRID 1635909 reaction equation
[C:1]1(C)[CH:6]=[CH:5][C:4](S(O)(=O)=O)=[CH:3][CH:2]=1.C1(=O)CCCCC1.[NH:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1>C1C=CC=CC=1>[C:1]1([N:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7967CyclohexanoneHCID 31268Pyrrolidine

Product 1

HCID 707681-Pyrrolidino-1-cyclohexene

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

1 g of para-toluenesulphonic acid is added to a mixture of 20 mmol of cyclohexanone and 22 mmol of pyrrolidine in 200 ml of dry benzene. The reaction mixture is stirred at reflux until, in the infra-red, the ketone has disappeared, with the enamine concomitantly appearing. The solvent is then evaporated off and the crude residue is purified by distillation in vacuo.

Workup

  1. customThe solvent is then evaporated off
  2. distillationthe crude residue is purified by distillation in vacuo

Sources & evidence

ORD record
ord-e98cda64668a44799b66ac12793026e3
Source dataset
uspto-grants-2003_01
Patent number
US06511992B2

Reaction notes

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