Lithium hydroxide, monohydrate → 21172-65-6

HRID 1361773Notes

Reaction equation

HRID 1361773 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][N:3]1[CH2:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15]C)=[O:14])=[CH:11][CH:10]=1.O.[OH-].[Li+]>CO.O>[O:1]=[C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][N:3]1[CH2:8][C:9]1[CH:10]=[CH:11][C:12]([C:13]([OH:15])=[O:14])=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 23144254HCID 23144254, compound

Product 1

HCID 2314438221172-65-6Yield 27%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Methyl 4-[(2-oxopiperidino)methyl]benzoate (2.47 g, 10.0 mmol) obtained in Step 1 was dissolved in a mixed solvent of methanol (30 mL) and water (10 mL), and 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 4-[(2-oxopiperidino)methyl]benzoic acid (629 mg. 27%).

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-d337a927e9ce4f0e8a1d7d82bc3d2312
Source dataset
uspto-grants-2011_02
Patent number
US07880013B2

Reaction notes

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