Sodium Hydroxide → 4-[4-(3-Cyclohexylpropyl)piperazin-1-yl]-2-fluorophenol

HRID 269899Notes

Reaction equation

HRID 269899 reaction equation
Cl.[CH:2]1([CH2:8][CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][C:20]([OH:23])=[C:19]([F:24])[CH:18]=3)[CH2:13][CH2:12]2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.C(=O)([O-])O.[Na+].[OH-].[Na+]>C(OCC)(=O)C>[CH:2]1([CH2:8][CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][C:20]([OH:23])=[C:19]([F:24])[CH:18]=3)[CH2:13][CH2:12]2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 231114144-[4-(3-Cyclohexylpropyl)piperazin-1-yl]-2-fluorophenol hydrochloride

Product 1

HCID 231114094-[4-(3-Cyclohexylpropyl)piperazin-1-yl]-2-fluorophenolYield 69.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-[4-(3-Cyclohexylpropyl)piperazin-1-yl]-2-fluorophenol hydrochloride (1.45 g) was suspended in ethyl acetate, and to which saturated aqueous sodium hydrogencarbonate solution and 2 grains of sodium hydroxide were added by the order stated, to effect distribution. The ethyl acetate layer was washed with saturated saline solution, dried over anhydrous magnesium sulfate, and the solvent was distilled off. Purifying the resulting crude product on silica gel column chromatography (eluent, chloroform: methanol=10:1), 4-[4-(3-cyclohexylpropyl)piperazin-1-yl]-2-fluorophenol (910 mg) was obtained.

Workup

  1. washThe ethyl acetate layer was washed with saturated saline solution
  2. dry with materialdried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off
  4. customPurifying the resulting crude product on silica gel column chromatography (eluent, chloroform: methanol=10:1)

Sources & evidence

ORD record
ord-853df0823b0b46e4a000ae41f5b8f83d
Source dataset
uspto-grants-2008_11
Patent number
US07449466B2

Reaction notes

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