Sulfuric Acid → Methyl 4-phenylpiperidine-4-carboxylate

HRID 322207

Reaction equation

HRID 322207 reaction equation
OS(O)(=O)=O.[CH3:6]C1C=CC(S(O)(=O)=O)=CC=1.[C:17]1([C:23]2([C:29]([OH:31])=[O:30])[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CO>[CH3:6][O:30][C:29]([C:23]1([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:24][CH2:25][NH:26][CH2:27][CH2:28]1)=[O:31]

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 stirred solution of H2SO4 (16 mL) in MeOH (400 mL), 4-phenyl-4-piperidinecarboxylic acid 4-methylbenzenesulfonate (37.7 g, 0.1 mole) was added and the mixture was stirred and refluxed for 8 hours. Excess methanol was evaporated at reduced pressure and the residue was poured into a mixture of ice and 6N NaOH. The pH was adjusted to 10-11 by adding more 6N NaOH and extracted with CH2Cl2 (3×150 mL). The combined CH2Cl2 extracts were dried (MgSO4) and the solvent evaporated to leave the desired product as a viscous oil. The 1H-NMR showed it to be pure (20.2 g, 92%) and was used without any further purification.

Workup

  1. temperaturerefluxed for 8 hours
  2. customExcess methanol was evaporated at reduced pressure
  3. additionthe residue was poured into a mixture of ice and 6N NaOH
  4. additionby adding more 6N NaOH
  5. extractionextracted with CH2Cl2 (3×150 mL)
  6. dry with materialThe combined CH2Cl2 extracts were dried (MgSO4)
  7. customthe solvent evaporated

Sources & evidence

ORD record
ord-9f18bf6108054f85bb18fdca7931b74f
Source dataset
uspto-grants-2001_04
Patent number
US06211198B1

Linked notes

Loading…