Hydrochloric Acid → 4-Pyrrolidin-1-yl-pentanoic acid

HRID 1695254Notes

Reaction equation

HRID 1695254 reaction equation
C[O:2][C:3](=[O:13])[CH2:4][CH2:5][CH:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1)[CH3:7].[OH-].[Na+].Cl>O>[N:8]1([CH:6]([CH3:7])[CH2:5][CH2:4][C:3]([OH:13])=[O:2])[CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 671897684-Pyrrolidin-1-yl-pentanoic acid methyl ester

Product 1

HCID 185240064-Pyrrolidin-1-yl-pentanoic acidYield 99.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of 4-pyrrolidin-l-yl-pentanoic acid methyl ester (2.0 g, 10.0 mmol) in water (20 mL), NaOH (0.8 g, 20.0 mmol, 2.0 eq) was added and the mixture was heated at reflux for 10 hours. The reaction was then allowed to cool to room temperature, the pH was adjusted to 3 with HCl 37% and the mixture was concentrated under reduced pressure. The residue was treated with EtOH, the sodium chloride precipitated was filtered off and the solvent was evaporated under reduced pressure, affording 1.7 g of the title compound as white solid (99% yield).

Workup

  1. additionwas added
  2. temperaturethe mixture was heated
  3. temperatureat reflux for 10 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. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-69eb03a8d6244070818fbe5445733327
Source dataset
uspto-grants-2012_04
Patent number
US08163729B2

Reaction notes

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