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Hydrochloric Acid → (4-{[4-(2-tert-Butylphenyl)piperazin-1-yl]carbonyl}-1H-imidazol-1-yl)acetic acid

HRID 534981
Notes
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Reaction equation

HRID 534981 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]([C:19]2[N:20]=[CH:21][N:22]([CH2:24][C:25]([O:27]C)=[O:26])[CH:23]=2)=[O:18])[CH2:13][CH2:12]1)([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-].Cl>O1CCCC1>[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]([C:19]2[N:20]=[CH:21][N:22]([CH2:24][C:25]([OH:27])=[O:26])[CH:23]=2)=[O:18])[CH2:13][CH2:12]1)([CH3:4])([CH3:2])[CH3:3]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 66751284Methyl (4-{[4-(2-tert-butylphenyl)piperazin-1-yl]carbonyl}-1H-imidazol-1-yl)acetate

Product 1

HCID 66792809(4-{[4-(2-tert-Butylphenyl)piperazin-1-yl]carbonyl}-1H-imidazol-1-yl)acetic acidYield 105.5%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Conditions

Temperature
0 °C

Procedure

A mixture of methyl (4-{[4-(2-tert-butylphenyl)piperazin-1-yl]carbonyl}-1H-imidazol-1-yl)acetate (Example 187, 0.34 g, 0.87 mmol) and 1M LiOH solution (5 mL, 5.0 mmol) in tetrahydrofuran (5 mL) was stirred at 0° C. for 2 h. The reaction mixture was acidified with 1 M HCl solution and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give the title compound (0.34 g, quant.) as a white powder.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-529ef9b4ea254d4da57fc250f0be1f52
Source dataset
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08853215B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes