Acetic Acid → 3-(Piperidin-1-yl)benzoic acid

HRID 2337Notes

Reaction equation

HRID 2337 reaction equation
[N:1]1([C:7]2[CH:8]=[C:9]([CH:14]=[CH:15][CH:16]=2)[C:10]([O:12]C)=[O:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O.[OH-].[Li+].C(O)(=O)C>O1CCOCC1.O>[N:1]1([C:7]2[CH:8]=[C:9]([CH:14]=[CH:15][CH:16]=2)[C:10]([OH:12])=[O:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 168937Lithium hydroxide, monohydrateHCID 7148413Methyl 3-(piperidin-1-yl)benzoate

Product 1

HCID 27955523-(Piperidin-1-yl)benzoic acidYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
40 °C

Procedure

The compound of Example 38 (540 mg, 2.466 mmol) was dissolved in dioxan (12 ml) and water (8 ml). Lithium hydroxide hydrate (300 mg, 7.143 mmol) was added and the mixture stirred at 40° C. for 1 h. The mixture was acidified with acetic acid, evaporated, azeotroped with toluene and chromatographed on silica (eluant 60/40/2, v/v/v, EtOAc/hexanes/AcOH) to provide a colourless solid (450 mg, 90%).

Workup

  1. customevaporated
  2. customazeotroped with toluene
  3. customchromatographed on silica (eluant 60/40/2, v/v/v, EtOAc/hexanes/AcOH)

Sources & evidence

ORD record
ord-227139b0204b412c8ef4f1e745340ffc
Source dataset
uspto-grants-1998_03
Patent number
US05728829

Reaction notes

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