Acetic Acid → 4-[4-(4-Octyloxyphenyl)piperazin-1-yl]benzoic acid

HRID 1386589Notes

Reaction equation

HRID 1386589 reaction equation
[CH2:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH2:21][CH2:20][N:19]([C:22]3[CH:29]=[CH:28]C(C#N)=[CH:24][CH:23]=3)[CH2:18][CH2:17]2)=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].O.[C:31]([OH:34])(=[O:33])[CH3:32]>OS(O)(=O)=O>[CH2:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH2:21][CH2:20][N:19]([C:22]3[CH:29]=[CH:28][C:32]([C:31]([OH:34])=[O:33])=[CH:24][CH:23]=3)[CH2:18][CH2:17]2)=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 211822454-[4-(4-Octyloxyphenyl)piperazin-1-yl]benzonitrile

Product 1

HCID 211824374-[4-(4-Octyloxyphenyl)piperazin-1-yl]benzoic acid

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 4-[4-(4-Octyloxyphenyl)piperazin-1-yl]benzonitrile (0.5 g) in 20% H2SO4 aqueous solution (30 ml) and acetic acid (20 ml) was refluxed for 9 hours. The reaction mixture was pulverized with water. The precipitate was collected by filtration, and added to a mixture of water, tetrahydrofuran and ethyl acetate, and adjusted to pH 2.5 with 1N NaOH aqueous solution. The organic layer was taken, and dried over magnesium sulfate. The magnesium sulfate was filtered off, and the filtrate was evaporated under reduced pressure to give 4-[4-(4-Octyloxyphenyl)piperazin-1-yl]benzoic acid (388 mg).

Workup

  1. filtrationThe precipitate was collected by filtration
  2. additionadded to a mixture of water, tetrahydrofuran and ethyl acetate
  3. dry with materialdried over magnesium sulfate
  4. filtrationThe magnesium sulfate was filtered off
  5. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-9fdcf6f81db1442c8545cabde755941a
Source dataset
uspto-grants-2001_07
Patent number
US06265536B1

Reaction notes

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