Water → 4-{4-[4-(3,3-Dimethyl-butyl)-piperazin-1-yl]-butoxy}-3-fluoro-benzoic acid

HRID 220912Notes

Reaction equation

HRID 220912 reaction equation
[OH-].[Na+].O.C([O:6][C:7](=[O:32])[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:21][CH2:20]2)=[C:10]([F:31])[CH:9]=1)C>O1CCOCC1>[CH3:28][C:27]([CH3:30])([CH3:29])[CH2:26][CH2:25][N:22]1[CH2:21][CH2:20][N:19]([CH2:18][CH2:17][CH2:16][CH2:15][O:14][C:11]2[CH:12]=[CH:13][C:8]([C:7]([OH:32])=[O:6])=[CH:9][C:10]=2[F:31])[CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 575553174-{4-[4-(3,3-Dimethyl-butyl)-piperazin-1-yl]-butoxy}-3-fluoro-benzoic Acid Ethyl Ester

Product 1

HCID 575553434-{4-[4-(3,3-Dimethyl-butyl)-piperazin-1-yl]-butoxy}-3-fluoro-benzoic acidYield 67%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Sodium hydroxide (0.5 g, 13.2 mmol) and water (5 ml) were added to a solution of 4-{4-[4-(3,3-dimethyl-butyl)-piperazin-1-yl]-butoxy}-3-fluoro-benzoic acid ethyl ester from Example E72.2 (1.35 g, 3.3 mmol) in dioxan (20 ml). The mixture was stirred for 1 h at room temperature then heated at 60° C. for 20 h. Solvents were concentrated in vacuo and azeotroped with toluene. The residue was purified by flash chromatography on silica gel (eluant; 1% 35% ammonia:19% methanol:80% chloroform) to yield the title compound (0.85 g, 67%).

Workup

  1. temperaturethen heated at 60° C. for 20 h
  2. concentrationSolvents were concentrated in vacuo
  3. customazeotroped with toluene
  4. customThe residue was purified by flash chromatography on silica gel (eluant; 1% 35% ammonia:19% methanol:80% chloroform)

Sources & evidence

ORD record
ord-7bb7ba162cd449bd8fadf504931e040b
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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