Hydrochloric Acid → 2-(Benzyloxy)-5-(piperidin-1-yl)benzoic acid

HRID 1623666Notes

Reaction equation

HRID 1623666 reaction equation
[Li+].[OH-].[C:3]1([CH2:9][O:10][C:11]2[CH:26]=[CH:25][C:24]([N:27]3[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]3)=[CH:23][C:12]=2[C:13]([O:15]CC2C=CC=CC=2)=[O:14])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl>C1COCC1.O.C(OCC)(=O)C>[C:3]1([CH2:9][O:10][C:11]2[CH:26]=[CH:25][C:24]([N:27]3[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]3)=[CH:23][C:12]=2[C:13]([OH:15])=[O:14])[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 66990101Benzyl 2-(benzyloxy)-5-(piperidin-1-yl)benzoate

Product 1

HCID 669910632-(Benzyloxy)-5-(piperidin-1-yl)benzoic acid

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

LiOH (1.25 mL, 3.74 mmol) was added to a stirred solution of phenylmethyl 2-[(phenylmethyl)oxy]-5-(1-piperidinyl)benzoate (may be prepared as described in Description 41; 150 mg, 0.37 mmol) in a mixture of THF:water (3:1, 10 ml). The mixture was heated to reflux for 12 h and then diluted with ethyl acetate (50 ml). 10% aqueous HCl was added to the mixture to adjust the pH to 2. The organic phase was isolated, washed with brine, dried over magnesium sulphate, and concentrated to give a yellow oil. The crude product was purified using Comflash to yield the title compound. 80 mg.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 12 h
  3. customThe organic phase was isolated
  4. washwashed with brine
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated
  7. customto give a yellow oil
  8. customThe crude product was purified

Sources & evidence

ORD record
ord-2761f3d84155469c83b5acc5ae5a4655
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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