Hydrochloric Acid → 1-{[4-(2-Tert-butylphenyl)piperazin-1-yl](oxo)acetyl}piperidine-4-carboxylic acid

HRID 534949Notes

Reaction equation

HRID 534949 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][N:14]([C:17](=[O:30])[C:18]([N:20]2[CH2:25][CH2:24][CH:23]([C:26]([O:28]C)=[O:27])[CH2:22][CH2:21]2)=[O:19])[CH2:13][CH2:12]1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+].Cl>C1COCC1>[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][N:14]([C:17](=[O:30])[C:18]([N:20]2[CH2:25][CH2:24][CH:23]([C:26]([OH:28])=[O:27])[CH2:22][CH2:21]2)=[O:19])[CH2:13][CH2:12]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 66751159Methyl 1-{[4-(2-tert-butylphenyl)piperazin-1-yl](oxo)acetyl}piperidine-4-carboxylate

Product 1

HCID 667513241-{[4-(2-Tert-butylphenyl)piperazin-1-yl](oxo)acetyl}piperidine-4-carboxylic acidYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 1-{[4-(2-tert-butylphenyl)piperazin-1-yl](oxo)acetyl}piperidine-4-carboxylate (Example 88, 0.159 g, 0.383 mmol) in THF (3 mL) stirring at 0° C. was added 1 M lithium hydroxide solution (3 mL, 3 mmol). After 2 h the reaction mixture was acidified with 1 M hydrochloric acid solution and extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4, and the solvent was evaporated under reduced pressure to provide 1-{[4-(2-tert-butylphenyl)piperazin-1-yl](oxo)acetyl}piperidine-4-carboxylic acid (0.147 g, 96%) as a white amorphous.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-0cd27e077c52466c80485f1caf7250c6
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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