Ammonium Hydroxide → 3-Cyclohexylpyrrolidin-2-one

HRID 1670812Notes

Reaction equation

HRID 1670812 reaction equation
[CH:1]1([CH:7]2[CH2:11][CH2:10][O:9][C:8]2=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[NH4+:14]>C(O)C>[CH:1]1([CH:7]2[CH2:11][CH2:10][NH:14][C:8]2=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 220132343-Cyclohexyl-dihydro-furan-2-one

Product 1

HCID 576579993-Cyclohexylpyrrolidin-2-oneYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Heat a mixture of 3-cyclohexyl-dihydro-furan-2-one (32.2 g), ammonium hydroxide (700 mL) and ethanol (700 mL) at 230° C. in a sealed steel bottle for 18 hours. Cool the reaction and remove the solvent in vacuo. Partition the residue with ethyl acetate (500 mL) and HCl (1N, 300 mL). Dry the organic over sodium sulfate. After filtration and concentration, recrystallize with 1:3 ethyl acetate:hexane to afford 30 grams (94%) of the title compound.

Workup

  1. temperatureHeat
  2. temperatureCool
  3. customthe reaction
  4. customremove the solvent in vacuo
  5. customPartition the residue with ethyl acetate (500 mL) and HCl (1N, 300 mL)
  6. dry with materialDry the organic over sodium sulfate
  7. filtrationAfter filtration and concentration
  8. customrecrystallize with 1:3 ethyl acetate

Sources & evidence

ORD record
ord-c2deaf126d1e4c1a91c00912e7ccb0ee
Source dataset
uspto-grants-2011_08
Patent number
US07994176B2

Reaction notes

Loading…