Sulfuric Acid → Normeperidine

HRID 322209

Reaction equation

HRID 322209 reaction equation
OS(O)(=O)=O.[CH3:6][C:7]1C=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>CCO>[CH2:6]([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])[CH3:7]

Participants

4

Reactant 2

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

Product 1

HCID 32414Normeperidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of H2SO4 (1.62 g, 16.56 mmol) in EtOH (200 mL), 4-phenyl-4-piperidinecarboxylic acid 4-methylbenzenesulfonate (25 g, 66.23 mmol) was added and the mixture was stirred and refluxed for 12 h. Excess ethanol 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 (3×100 mL). The combined CH2Cl2 extracts were dried (MgSO4) and the solvent evaporated to leave the desired product as a colorless viscous oil, the 1H-NMR showed it to be pure (14.68 g, 95%) and was used without any further purification.

Workup

  1. temperaturerefluxed for 12 h
  2. customExcess ethanol 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 (3×100 mL)
  6. dry with materialThe combined CH2Cl2 extracts were dried (MgSO4)
  7. customthe solvent evaporated

Sources & evidence

ORD record
ord-9e830065fade41d9abd2c9b82a2b57ef
Source dataset
uspto-grants-2001_04
Patent number
US06211198B1

Linked notes

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