Ethanol → 2,2-Dimethyl-N-(2-morpholin-4-yl-ethyl)-malonamic acid

HRID 924626Notes

Reaction equation

HRID 924626 reaction equation
C([O:3][C:4](=[O:19])[C:5]([CH3:18])([CH3:17])[C:6]([NH:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1)=[O:7])C.[OH-].[K+].C(O)C>O>[CH3:17][C:5]([CH3:18])([C:6]([NH:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1)=[O:7])[C:4]([OH:19])=[O:3]

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 688020542,2-Dimethyl-N-(2-morpholin-4-yl-ethyl)-Malonamic Acid Ethyl Ester

Product 1

HCID 688041692,2-Dimethyl-N-(2-morpholin-4-yl-ethyl)-malonamic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

34.1 g 2,2-Dimethyl-N-(2-morpholin-4-yl-ethyl)-malonamic acid ethyl ester, 8.4 g potassium hydroxide, 200 ml ethanol and 4.5 ml H2O were stirred at 80° C. for 6 hours. Then most of the solvent was removed and the pH was adjusted to pH 3-4 with about 100 ml 2N HCl. The solvent was evaporated and toluol was added and then removed. To the final residue methanol was added and the suspension was filtered to remove salts. The solvent was removed and the residue was dissolved in H2O and lyophilized. The product was characterized by 1H-NMR.

Workup

  1. customThen most of the solvent was removed
  2. customThe solvent was evaporated
  3. additiontoluol was added
  4. customremoved
  5. additionTo the final residue methanol was added
  6. filtrationthe suspension was filtered
  7. customto remove salts
  8. customThe solvent was removed
  9. dissolutionthe residue was dissolved in H2O

Sources & evidence

ORD record
ord-0d2a51659a5e441d898194151846db89
Source dataset
uspto-grants-2016_03
Patent number
US09283186B2

Reaction notes

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