Lithium hydroxide, monohydrate → 1-(dimethylcarbamoyl)piperidine-4-carboxylic acid

HRID 1967745Notes

Reaction equation

HRID 1967745 reaction equation
[CH3:1][N:2]([CH3:16])[C:3]([N:5]1[CH2:10][CH2:9][CH:8]([C:11]([O:13]CC)=[O:12])[CH2:7][CH2:6]1)=[O:4].O.[OH-].[Li+]>CO.O>[CH3:1][N:2]([CH3:16])[C:3]([N:5]1[CH2:10][CH2:9][CH:8]([C:11]([OH:13])=[O:12])[CH2:7][CH2:6]1)=[O:4]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 1829960ethyl 1-(dimethylcarbamoyl)piperidine-4-carboxylate

Product 1

HCID 50764741-(dimethylcarbamoyl)piperidine-4-carboxylic acidYield 42%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Ethyl 1-(N,N-dimethylcarbamoyl)piperidine-4-carboxylate (2.28 g, 10.0 mmol) obtained in Step 1 was dissolved in a mixed solvent of methanol (30 mL) and water (10 mL), lithium hydroxide monohydrate (2.10 g, 50.0 mmol) was added thereto, followed by stirring at room temperature for 30 minutes. The reaction mixture was concentrated under reduced pressure, and 6 mol/L hydrochloric acid was added to the resulting residue to adjust the pH to 1, followed by extraction with chloroform. The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was distilled away under reduced pressure to afford 1-(N,N-dimethylcarbamoyl)piperidine-4-carboxylic acid (830 mg, 42%).

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated under reduced pressure, and 6 mol/L hydrochloric acid
  3. additionwas added to the resulting residue
  4. extractionfollowed by extraction with chloroform
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-6660b62aa6b9460c964b345870e1f15e
Source dataset
uspto-grants-2013_04
Patent number
US08420827B2

Reaction notes

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