Iodoethane → 1-Ethylpiperidine-4-carboxylic acid

HRID 1963700

Reaction equation

HRID 1963700 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)=[O:5])C.I[CH2:13][CH3:14].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH2:13]([N:9]1[CH2:8][CH2:7][CH:6]([C:4]([OH:3])=[O:5])[CH2:11][CH2:10]1)[CH3:14]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 70770Ethyl 4-piperidinecarboxylate

Product 1

HCID 187837731-Ethylpiperidine-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To ethylpiperidine-4-carboxylate (1 eq) in ethanol was added iodoethane (1.1 eq) and potassium carbonate (2 eq) and the resulting mixture was refluxed for 16 h. The mixture was then cooled to room temperature and filtered. Ethanol was concentrated and partitioned between methylene chloride and water. The organic layer was then washed with saturated sodium chloride solution, dried with sodium sulfate and concentrated. To it was then added concentrated hydrochloric acid and water (2:1) and the mixture was refluxed for 5 h. The resulting 1-(ethyl)piperidine-4-carboxylic acid was then azeotroped with toluene. MS: MH+=158.

Workup

  1. temperaturethe resulting mixture was refluxed for 16 h
  2. filtrationfiltered
  3. concentrationEthanol was concentrated
  4. custompartitioned between methylene chloride and water
  5. washThe organic layer was then washed with saturated sodium chloride solution
  6. dry with materialdried with sodium sulfate
  7. concentrationconcentrated
  8. additionTo it was then added concentrated hydrochloric acid and water (2:1)
  9. temperaturethe mixture was refluxed for 5 h
  10. customThe resulting 1-(ethyl)piperidine-4-carboxylic acid was then azeotroped with toluene

Sources & evidence

ORD record
ord-360b3805a976473bbc9dc1131933b8a2
Source dataset
uspto-grants-2013_04
Patent number
US08415382B2

Linked notes

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