Sodium Hydroxide → 2-Piperidinecarboxylic acid, 1-benzoyl-2-methyl-

HRID 1770101Notes

Reaction equation

HRID 1770101 reaction equation
C([O:3][C:4]([C:6]1([CH3:20])[CH2:11][CH2:10][CH2:9][CH2:8][N:7]1[C:12](=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:5])C.[OH-].[Na+]>CCO.O>[C:12]([N:7]1[CH2:8][CH2:9][CH2:10][CH2:11][C:6]1([CH3:20])[C:4]([OH:5])=[O:3])(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 20095410HCID 20095410, compound

Product 1

HCID 200954122-Piperidinecarboxylic acid, 1-benzoyl-2-methyl-Yield 22%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

Ethyl-1-benzoyl-2-methyl-piperidine-2-carboxylate (6.49 g, 23.51 mmol) was dissolved in EtOH (54 mL) and H2O (16 mL). NaOH (2.75 g, 68.6 mmol) was added and the reaction was heated to 40° C. for 1 h. An additional portion of NaOH (2.75 g, 68.6 mmol) was added and the reaction was heated to 65° C. for 1 h. The ethanol was removed and the residue was diluted with 50 mL of H2O. The pH was adjusted to ~2 with HCl (c). The aqueous layer was extracted 3× with ether and ethyl acetate. Removal of solvent provided 0.75 g, 22% yield of 1-benzoyl-2-methyl-piperidine-2-carboxylic acid. 1H NMR (200 MHz, DMSO) δ1.4 (s, 3H), 1.5-1.9 (comp m, 4H), 3.0 (m, 2H), 3.4 (m, 2H), 7.4 (m, 5H).

Workup

  1. temperaturethe reaction was heated to 65° C. for 1 h
  2. customThe ethanol was removed
  3. additionthe residue was diluted with 50 mL of H2O
  4. extractionThe aqueous layer was extracted 3× with ether and ethyl acetate
  5. customRemoval of solvent

Sources & evidence

ORD record
ord-858e1749802f46a49c1506111b6ce3b4
Source dataset
uspto-grants-1995_01
Patent number
US05385908

Reaction notes

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