Methanol → Methyl 4-(piperidin-4-yl)benzoate

HRID 478640Notes

Reaction equation

HRID 478640 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.[CH3:16]O>>[CH3:16][O:12][C:11](=[O:13])[C:10]1[CH:14]=[CH:15][C:7]([CH:4]2[CH2:5][CH2:6][NH:1][CH2:2][CH2:3]2)=[CH:8][CH:9]=1

Participants

3

Reactant 2

HCID 887MethanolHCID 180024624-(Piperidin-4-yl)benzoic acid

Product 1

HCID 24904226Methyl 4-(piperidin-4-yl)benzoate

Procedure

4-Piperidin-4-yl-benzoic acid (47 mmol) is dissolved in methanol (300 ml) and 1 ml of concentrated sulfonic acid is added. The mixture is heated under reflux overnight. After evaporation of the solvent, the residue is dissolved in a mixture of water and sodium carbonate (to ensure basic conditions) and extracted three times with ethyl acetate. The combined extract is dried over sodium sulfate and evaporated. A brown powder with Rf=0.18 (CH2Cl2/MeOH=9:1) is obtained.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux overnight
  3. customAfter evaporation of the solvent
  4. dissolutionthe residue is dissolved in a mixture of water and sodium carbonate (to ensure basic conditions)
  5. extractionextracted three times with ethyl acetate
  6. extractionThe combined extract
  7. dry with materialis dried over sodium sulfate
  8. customevaporated
  9. customA brown powder with Rf=0.18 (CH2Cl2/MeOH=9:1) is obtained

Sources & evidence

ORD record
ord-10bb8a05683e45f7a5dd016b41686167
Source dataset
uspto-grants-2003_11
Patent number
US06642239B2

Reaction notes

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