Cyclohexanone → 1-Pyrrolidino-1-cyclohexene

HRID 2064546Notes

Reaction equation

HRID 2064546 reaction equation
[C:1]1(=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1>C1(C)C=CC=CC=1>[C:1]1([N:8]2[CH2:12][CH2:11][CH2:10][CH2:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

4

Reactant 2

HCID 7967CyclohexanoneHCID 31268Pyrrolidine

Product 1

HCID 707681-Pyrrolidino-1-cyclohexeneYield 102%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A 50 mL round-bottomed flask containing cyclohexanone (3.82 g, 39 mmol) in anhydrous toluene (20 mL) was fitted with a Dean-Stark trap containing 3 Å molecular sieves, reflux condenser and a heating mantle, pyrrolidine (6.00 mL) was added, and the solution heated to reflux for 18 h. The solvent was evaporated and the crude product 1-cyclohex-1-en-1-ylpyrrolidine was used directly for the next reaction. (6.0 g, 102% yield, 95% purity by HPLC). MS(ESI+): 152.3; MS(ESI−): 150.1.

Workup

  1. customwas fitted with a Dean-Stark trap
  2. additioncontaining 3 Å molecular sieves
  3. temperaturereflux condenser
  4. temperaturethe solution heated
  5. temperatureto reflux for 18 h
  6. customThe solvent was evaporated
  7. customthe crude product 1-cyclohex-1-en-1-ylpyrrolidine was used directly for the next reaction

Sources & evidence

ORD record
ord-4c299df149274e188c2add04db02654d
Source dataset
uspto-grants-2012_10
Patent number
US08288432B2

Reaction notes

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