Sulfuric Acid → Methyl 4-phenylpiperidine-4-carboxylate

HRID 2189979Notes

Reaction equation

HRID 2189979 reaction equation
[C:1]1(C)C=CC(S(O)(=O)=O)=CC=1.[C:12]1([C:18]2([C:24]([OH:26])=[O:25])[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.S(=O)(=O)(O)O>CO>[CH3:1][O:25][C:24]([C:18]1([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:19][CH2:20][NH:21][CH2:22][CH2:23]1)=[O:26]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 27236574-Piperidinecarboxylic acid, 4-phenyl-, 4-methylbenzenesulfonate (1:1)

Product 1

HCID 545827Methyl 4-phenylpiperidine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-phenyl-piperidine-4-carboxylic acid 4-toluene sulfonate (3.0 g, 0.008, mol) in methanol was added sulfuric acid (1.28 mL, 0.023 mol) and heated under reflux for 12 h. Excess methanol was evaporated and the residue poured into a cooled mixture of ice and 32% aqueous NaOH (if necessary adjust pH to >10). The aqueous phase was extracted with DCM, the combined organic phases were dried over Na2SO4 and the solvent was evaporated. The residue was evaporated several times with toluene and used crude for the next reaction.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 12 h
  3. customExcess methanol was evaporated
  4. additionthe residue poured into a cooled mixture of ice and 32% aqueous NaOH (if necessary adjust pH to >10)
  5. extractionThe aqueous phase was extracted with DCM
  6. dry with materialthe combined organic phases were dried over Na2SO4
  7. customthe solvent was evaporated
  8. customThe residue was evaporated several times with toluene
  9. customfor the next reaction

Sources & evidence

ORD record
ord-8b8e2cafa91c421abe85105a133753ab
Source dataset
uspto-grants-2012_12
Patent number
US08324250B2

Reaction notes

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