Hydrochloric Acid → HCID 20991772, compound

HRID 1695227Notes

Reaction equation

HRID 1695227 reaction equation
C([O:3][C:4](=[O:16])[CH2:5][CH2:6][CH2:7][N:8]1[CH:13]([CH3:14])[CH2:12][CH2:11][CH2:10][CH:9]1[CH3:15])C.[OH-].[Na+].Cl>O.CO>[CH3:14][CH:13]1[CH2:12][CH2:11][CH2:10][CH:9]([CH3:15])[N:8]1[CH2:7][CH2:6][CH2:5][C:4]([OH:16])=[O:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 19867685HCID 19867685, compound

Product 1

HCID 20991772HCID 20991772, compoundYield 71.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a suspension of 4-(2,6-dimethyl-piperidin-1-yl)-butyric acid ethyl ester (1.5 g, 6.7 mmol) in water (5 mL) and MeOH (1 mL), NaOH (266 mg, 6.7 mmol, 1.0 eq) was added and the mixture was heated at reflux for 22 hours. The reaction was then allowed to cool down to room temperature, the pH adjusted to 4 at 0° C. with HCl 2N and the mixture was concentrated under reduced pressure. The residue was treated with EtOH, and the sodium chloride precipitated was filtered off. Evaporation of the solvent under reduced pressure afforded 950 mg of the title compound as a white solid (51% yield).

Workup

  1. additionwas added
  2. temperaturethe mixture was heated
  3. temperatureat reflux for 22 hours
  4. concentrationthe mixture was concentrated under reduced pressure
  5. additionThe residue was treated with EtOH
  6. customthe sodium chloride precipitated
  7. filtrationwas filtered off
  8. customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-dd39ca99f0dd48329f1beb640dfa5636
Source dataset
uspto-grants-2012_04
Patent number
US08163729B2

Reaction notes

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