Lithium hydroxide, monohydrate → 4-{3-[4-(3,3-Dimethyl-butyl)-piperazin-1-yl]-3-oxo-propyl}-3-methyl-benzoic Acid

HRID 220861Notes

Reaction equation

HRID 220861 reaction equation
O.[OH-].[Li+].C[O:5][C:6](=[O:30])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][C:15]([N:17]2[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:19][CH2:18]2)=[O:16])=[C:9]([CH3:29])[CH:8]=1>C1COCC1.O>[CH3:26][C:25]([CH3:28])([CH3:27])[CH2:24][CH2:23][N:20]1[CH2:21][CH2:22][N:17]([C:15](=[O:16])[CH2:14][CH2:13][C:10]2[CH:11]=[CH:12][C:7]([C:6]([OH:30])=[O:5])=[CH:8][C:9]=2[CH3:29])[CH2:18][CH2:19]1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 575554114-{3-[4-(3,3-Dimethyl-butyl)-piperazin-1-yl]-3-oxo-propyl}-3-methyl-benzoic Acid Methyl Ester

Product 1

HCID 575552774-{3-[4-(3,3-Dimethyl-butyl)-piperazin-1-yl]-3-oxo-propyl}-3-methyl-benzoic AcidYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide monohydrate (2.4 g, 56.7 mmol) was added to a solution of 4-{3-[4-(3,3-dimethyl-butyl)-piperazin-1-yl]-3-oxo-propyl}-3-methyl-benzoic acid methyl ester from Example E44.1 (8.5 g, 22.7 mmol) in THF (200 ml) and water (100 ml). The mixture was stirred for 24 h at room temperature then solvents were removed in vacuo. The residue was purified by flash chromatography on silica gel (eluant; 2% acetic acid:4% methanol:94% dichloromethane) to yield the title compound (8.1 g, 99%).

Workup

  1. customsolvents were removed in vacuo
  2. customThe residue was purified by flash chromatography on silica gel (eluant; 2% acetic acid:4% methanol:94% dichloromethane)

Sources & evidence

ORD record
ord-b4a4fb8609f8468bb40e81db9ec88c00
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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