Lithium Hydroxide → 2-Methoxy-4-(1-acetyl-4-piperidyloxy)phenylacetic acid

HRID 1292344Notes

Reaction equation

HRID 1292344 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH:10]2[CH2:15][CH2:14][N:13]([C:16](=[O:18])[CH3:17])[CH2:12][CH2:11]2)[CH:6]=[CH:5][C:4]=1[CH2:19][C:20]([O:22]C)=[O:21].[OH-].[Li+]>C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH:10]2[CH2:15][CH2:14][N:13]([C:16](=[O:18])[CH3:17])[CH2:12][CH2:11]2)[CH:6]=[CH:5][C:4]=1[CH2:19][C:20]([OH:22])=[O:21]

Participants

4

Reactant 2

HCID 3939Lithium Hydroxide2×HCID 18914188Methyl 2-methoxy-4-(1-acetyl-4-piperidyloxy)phenylacetate

Product 1

HCID 537598172-Methoxy-4-(1-acetyl-4-piperidyloxy)phenylacetic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-methoxy-4-(1-acetyl-4-piperidyloxy)phenylacetate (0.18 g, 0.56 mmol) was dissolved in THF (5 ml) and treated with lithium hydroxide (0.67 ml of a 1M aqueous solution, 0.67 mmol). The mixture was stirred at ambient temperature for 4 hours, then treated with an additional 0.2 ml of 1M lithium hydroxide. The mixture was heated at 60° for 6 hours, then cooled and concentrated in vacuo. The residue was acidified with 1M HCl, and extracted with ethyl acetate. The combined ethyl acetate layers were extracted with saturated aqueous sodium carbonate. The combined sodium carbonate layers were acidified with concentrated HCl and extracted with ethyl acetate. The combined ethyl acetate layers were dried over sodium sulfate, filtered, and evaporated to dryness in vacuo to give 2-methoxy-4-(1-acetyl-4-piperidyloxy)phenyl-acetic acid.

Workup

  1. temperatureThe mixture was heated at 60° for 6 hours
  2. temperaturecooled
  3. concentrationconcentrated in vacuo
  4. extractionextracted with ethyl acetate
  5. extractionThe combined ethyl acetate layers were extracted with saturated aqueous sodium carbonate
  6. extractionextracted with ethyl acetate
  7. dry with materialThe combined ethyl acetate layers were dried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-90839923fbbd4f508f8b3c0bef255199
Source dataset
uspto-grants-1998_05
Patent number
US05756504

Reaction notes

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