Sodium Hydroxide → 4-{2-[4-(3,3-Dimethyl-butyl)-piperazin-1-yl]-ethoxy}-3-methyl-benzoic Acid

HRID 220845Notes

Reaction equation

HRID 220845 reaction equation
C[O:2][C:3](=[O:26])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:15][CH2:14]2)=[C:6]([CH3:25])[CH:5]=1.[OH-].[Na+]>O1CCOCC1>[CH3:22][C:21]([CH3:24])([CH3:23])[CH2:20][CH2:19][N:16]1[CH2:17][CH2:18][N:13]([CH2:12][CH2:11][O:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:26])=[O:2])=[CH:5][C:6]=2[CH3:25])[CH2:14][CH2:15]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 575552114-{2-[4-(3,3-Dimethyl-butyl)-piperazin-1-yl]-ethoxy}-3-methyl-benzoic Acid Methyl Ester

Product 1

HCID 575552124-{2-[4-(3,3-Dimethyl-butyl)-piperazin-1-yl]-ethoxy}-3-methyl-benzoic AcidYield 100%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4-{2-[4-(3,3-Dimethyl-butyl)-piperazin-1-yl]-ethoxy}-3-methyl-benzoic acid methyl ester from Example E40.3 (42 mg, 0.12 mmol) was dissolved in dioxan (5 ml) and 1M NaOH (1 ml) was added. The mixture was heated at reflux for 2 h then solvents were concentrated in vacuo. The residue was dissolved in EtOAc, washed with saturated NaHCO3, water then brine, dried and concentrated in vacuo to yield the title compound (40 mg, 100%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 h
  3. concentrationsolvents were concentrated in vacuo
  4. dissolutionThe residue was dissolved in EtOAc
  5. washwashed with saturated NaHCO3, water
  6. dry with materialbrine, dried
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5bbdb2fd072b44be97f61975105033dd
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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