Toluene → 1-(4-Propylcyclohex-1-enyl)pyrrolidine

HRID 1257942Notes

Reaction equation

HRID 1257942 reaction equation
C1(C)C=CC=CC=1.[NH:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1.[CH2:13]([CH:16]1[CH2:21][CH2:20][C:19](=O)[CH2:18][CH2:17]1)[CH2:14][CH3:15]>O>[CH2:13]([CH:16]1[CH2:21][CH2:20][C:19]([N:8]2[CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:18][CH2:17]1)[CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 1140TolueneHCID 31268PyrrolidineHCID 1424824-Propylcyclohexanone

Product 1

HCID 227090491-(4-Propylcyclohex-1-enyl)pyrrolidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Toluene (200 ml) and pyrrolidine (90 ml) were added to 4-propylcyclohexanone (53.0 g) in a reaction vessel equipped with a Dean-Stark apparatus under an atmosphere of nitrogen. The mixture was refluxed for 3 hours while the water formed was removed by a Dean-Stark apparatus. After the reaction mixture had been cooled to a room temperature, it was washed with brine, and dried over anhydrous magnesium sulfate. The toluene was distilled off under reduced pressure to give 1-(4-propylcyclohex-1-enyl)pyrrolidine (58.2 g).

Workup

  1. customequipped with a Dean-Stark apparatus under an atmosphere of nitrogen
  2. customformed
  3. customwas removed by a Dean-Stark apparatus
  4. washit was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe toluene was distilled off under reduced pressure

Sources & evidence

ORD record
ord-3a9b64e2a2214bb6b317e411e8838b39
Source dataset
uspto-grants-2013_06
Patent number
US08465674B2

Reaction notes

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