Ethyl Acetate → (3s, 5r)-1-(2,4-Dimethoxy-benzyl)-3,5-dimethyl-piperazin-2-one

HRID 1432906Notes

Reaction equation

HRID 1432906 reaction equation
[CH3:1][O:2][C:3]1[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[CH:21][C:4]=1[CH2:5][N:6]1[CH2:11][C@@H:10]([CH3:12])[N:9](C(=O)C(F)(F)F)[C@@H:8]([CH3:19])[C:7]1=[O:20].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CO.O>[CH3:1][O:2][C:3]1[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[CH:21][C:4]=1[CH2:5][N:6]1[CH2:11][C@@H:10]([CH3:12])[NH:9][C@@H:8]([CH3:19])[C:7]1=[O:20]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 57171471(3S, 5R)-1-(2,4-dimethoxy-benzyl)-3,5-dimethyl-4-trifluoroacetyl-piperazin-2-one

Product 1

HCID 90816299(3s, 5r)-1-(2,4-Dimethoxy-benzyl)-3,5-dimethyl-piperazin-2-oneYield 91%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

(3S, 5R)-1-(2,4-Dimethoxy-benzyl)-3,5-dimethyl-4-trifluoroacetyl-piperazin-2-one (575 mg, 1.54 mmol) is dissolved in 30 mL of methanol and 3 mL of H2O. Potassium carbonate (883 mg, 6.4 mmol) is added to the solution, and the reaction is refluxed for one and half hours before concentration. Ethyl acetate (3×50 mL) is used to extract the aqueous layer. Removal of Ethyl acetate afforded the crude amine (387 mg, 91% yield) as a clear oil. C15H22N2O3 MS m/z: 279.

Workup

  1. temperaturethe reaction is refluxed for one and half hours before concentration
  2. extractionto extract the aqueous layer
  3. customRemoval of Ethyl acetate

Sources & evidence

ORD record
ord-0dfd7411a8694bc0ac4aa37e7b0dabc9
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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