Potassium Carbonate → 1-(2-Methoxyethyl)piperidine-4-carboxylic acid

HRID 30785Notes

Reaction equation

HRID 30785 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)=[O:5])C.Br[CH2:13][CH2:14][O:15][CH3:16].C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+]>C(O)C.O>[CH3:16][O:15][CH2:14][CH2:13][N:9]1[CH2:8][CH2:7][CH:6]([C:4]([OH:3])=[O:5])[CH2:11][CH2:10]1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 70770Ethyl 4-piperidinecarboxylateHCID 809722-Bromoethyl methyl ether

Product 1

HCID 221853841-(2-Methoxyethyl)piperidine-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

To ethylpiperidine-4-carboxylate (1 eq) in ethanol was added 2-bromo-1-methoxyethane (1 eq) and potassium carbonate 2 eq) and the resulting mixture was refluxed for 16 h. The mixture was then filtered and concentrated. To it was then added ethanol and water (3:1) and sodium hydroxide (1 eq) and it was refluxed for 16 h. The resulting 1-(2-methoxyethyl)piperidine-4-carboxylic acid was then azeotroped with toluene. MS: MH+=188.

Workup

  1. temperaturewas refluxed for 16 h
  2. filtrationThe mixture was then filtered
  3. concentrationconcentrated
  4. customThe resulting 1-(2-methoxyethyl)piperidine-4-carboxylic acid was then azeotroped with toluene

Sources & evidence

ORD record
ord-c6bc3d51d5ce4044b0b19457b0cfd333
Source dataset
uspto-grants-2008_09
Patent number
US07423150B2

Reaction notes

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