Pyrrolidine → 1-(4-Benzyl-cyclohex-1-enyl)-pyrrolidine

HRID 840615Notes

Reaction equation

HRID 840615 reaction equation
[CH2:1]([CH:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH2:1]([CH:8]1[CH2:13][CH2:12][C:11]([N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[CH:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 521998p-Toluenesulfonic acid monohydrateHCID 106552354-Benzylcyclohexanone

Product 1

HCID 226201201-(4-Benzyl-cyclohex-1-enyl)-pyrrolidine

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 5 g of 4-benzyl-cyclohexanone, 3.5 g of pyrrolidine, 500 mL of benzene and 10 mg of p-toluenesulfonic acid monohydrate was heated under a water separator apparatus for 48 h, removing the distillate periodically until there was about 50 mL remaining. The solution was cooled and concentrated to 8 g of an amber liquid. The NMR was consistent with complete conversion to the enamine.

Workup

  1. temperaturewas heated under a water separator apparatus for 48 h
  2. customremoving the distillate periodically until there
  3. temperatureThe solution was cooled
  4. concentrationconcentrated to 8 g of an amber liquid

Sources & evidence

ORD record
ord-d08f1c2735d64bb69eb2dc9befcd5e8c
Source dataset
uspto-grants-2002_04
Patent number
US06369076B1

Reaction notes

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