Ethyl 4-(morpholin-4-yl)butanoate → 4-Morpholinebutanoic acid

HRID 1695199Notes

Reaction equation

HRID 1695199 reaction equation
C([O:3][C:4](=[O:14])[CH2:5][CH2:6][CH2:7][N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)C>[OH-].[Na+]>[N:8]1([CH2:7][CH2:6][CH2:5][C:4]([OH:14])=[O:3])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1

Participants

3

Reactant 1

HCID 13191881Ethyl 4-(morpholin-4-yl)butanoate

Product 1

HCID 798724-Morpholinebutanoic acidYield 73.9%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

4-Morpholin-4-yl-butyric acid ethyl ester (about 25 mmol) was suspended in 100 mL of NaOH 10%, and the mixture was heated at reflux for 10 hours. The reaction mixture was then allowed to cool down to room temperature and washed with AcOEt. The aqueous layer was recovered by extraction and acidified at 0° C. with HCl 37% to pH 4 and concentrated under reduced pressure. The residue was treated with EtOH and the sodium chloride which precipitated was filtered off. The crude was treated with acetone and filtered; evaporation of the solvent under reduced pressure afforded 3.2 g of the title compound as a white solid in 72% overall yield of steps a) and b).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 10 hours
  3. washwashed with AcOEt
  4. customThe aqueous layer was recovered by extraction
  5. customacidified at 0° C. with HCl 37% to pH 4
  6. concentrationconcentrated under reduced pressure
  7. additionThe residue was treated with EtOH
  8. customthe sodium chloride which precipitated
  9. filtrationwas filtered off
  10. additionThe crude was treated with acetone
  11. filtrationfiltered
  12. customevaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-1eddf63f4f524b77bd998f0a51e944ed
Source dataset
uspto-grants-2012_04
Patent number
US08163729B2

Reaction notes

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