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

HRID 989062Notes

Reaction equation

HRID 989062 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-d9635ccb5bb2497f8be6f627e60b1149
Source dataset
uspto-grants-2003_10
Patent number
US06638946B2

Reaction notes

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