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

HRID 220859Notes

Reaction equation

HRID 220859 reaction equation
O.[OH-].[Li+].C[O:5][C:6](=[O:31])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][C:16]([N:18]2[CH2:23][CH2:22][N:21]([CH2:24][CH2:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:20][CH2:19]2)=[O:17])=[C:9]([CH3:30])[CH:8]=1>C1COCC1.O>[CH3:27][C:26]([CH3:29])([CH3:28])[CH2:25][CH2:24][N:21]1[CH2:22][CH2:23][N:18]([C:16](=[O:17])[CH2:15][CH2:14][CH2:13][C:10]2[CH:11]=[CH:12][C:7]([C:6]([OH:31])=[O:5])=[CH:8][C:9]=2[CH3:30])[CH2:19][CH2:20]1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 575554194-{4-[4-(3,3-Dimethyl-butyl)-piperazin-1-yl]-4-oxo-butyl}-3-methyl-benzoic Acid Methyl Ester

Product 1

HCID 575552274-{4-[4-(3,3-Dimethyl-butyl)-piperazin-1-yl]-4-oxo-butyl}-3-methyl-benzoic AcidYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide monohydrate (108 mg, 2.6 mmol) was added to a solution of 4-{4-[4-(3,3-dimethyl-butyl)-piperazin-1-yl]-4-oxo-butyl}-3-methyl-benzoic acid methyl ester from Example E43.1 (500 mg, 1.3 mmol) in THF (12 ml) and water (6 ml). The mixture was stirred for 20 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) then recrystallised from chloroform and pet. ether to yield the title compound (439 mg, 91%).

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)
  3. customthen recrystallised from chloroform and pet. ether

Sources & evidence

ORD record
ord-73c94afa55a74b1bbb78b46db4012ac8
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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