HCID 86752428, compound → Benzeneacetic acid, 2-[3-(1-pyrrolidinyl)propoxy]-

HRID 1599162Notes

Reaction equation

HRID 1599162 reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH2:16][C:17]([O:19]CC2C=CC=CC=2)=[O:18])[CH2:5][CH2:4][CH2:3][CH2:2]1>C(OCC)(=O)C.ClCCl.[OH-].[OH-].[Pd+2]>[N:1]1([CH2:6][CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH2:16][C:17]([OH:19])=[O:18])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 1

HCID 86752428HCID 86752428, compound

Product 1

HCID 11108172Benzeneacetic acid, 2-[3-(1-pyrrolidinyl)propoxy]-Yield 73.4%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

0.8 g of 10% palladium hydroxide on carbon is added to a solution of 5.3 g of benzyl {2-[3-(1-pyrrolidinyl)propoxy]phenyl}acetate in 50 cm3 of ethyl acetate and 50 cm3 of dichloromethane, and the mixture is heated to 50° C. and then purged with nitrogen. After hydrogen has been bubbled through for 20 hours, the suspension is cooled to room temperature and purged with a stream of nitrogen, then filtered and concentrated to dryness under reduced pressure (2.7 kPa). The oily residue obtained is chromatographed on an alumina column (particle size 100 mesh, height 30 cm, diameter 4.5 cm), eluting under a pressure of 0.7 bar of nitrogen with a mixture of cyclohexane and ethyl acetate (75:25 by volume) and collecting fractions of 100 cm3. Fractions 1 to 6 are concentrated to dryness under reduced pressure (2.7 kPa). 2.9 g of {2-[3-(1-pyrrolidinyl)propoxy]phenyl}acetic acid are obtained in the form of a thick oil.

Workup

  1. custompurged with nitrogen
  2. customAfter hydrogen has been bubbled through for 20 hours
  3. temperaturethe suspension is cooled to room temperature
  4. custompurged with a stream of nitrogen
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  7. customThe oily residue obtained
  8. customis chromatographed on an alumina column (particle size 100 mesh, height 30 cm, diameter 4.5 cm)
  9. washeluting under a pressure of 0.7 bar of nitrogen with a mixture of cyclohexane and ethyl acetate (75:25 by volume)
  10. customcollecting fractions of 100 cm3
  11. concentrationFractions 1 to 6 are concentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-6ef8770355f44fc2b4b3618f8badf5eb
Source dataset
uspto-grants-1998_04
Patent number
US05739351

Reaction notes

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