3,5-Di-tert-butyl-4-hydroxybenzoic acid → 1-Benzyl-4-(3,5-di-t-butyl-4-hydroxy-benzoyl)piperazine

HRID 48925

Reaction equation

HRID 48925 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:13]=1[OH:14])[C:8]([OH:10])=O)([CH3:4])([CH3:3])[CH3:2].[CH2:19]([N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.Cl.CN(C)CCCN=C=NCC>ClCCl>[CH2:19]([N:26]1[CH2:31][CH2:30][N:29]([C:8](=[O:10])[C:7]2[CH:11]=[C:12]([C:15]([CH3:16])([CH3:17])[CH3:18])[C:13]([OH:14])=[C:5]([C:1]([CH3:3])([CH3:2])[CH3:4])[CH:6]=2)[CH2:28][CH2:27]1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 150073,5-Di-tert-butyl-4-hydroxybenzoic acidHCID 759941-BenzylpiperazineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 143003101-Benzyl-4-(3,5-di-t-butyl-4-hydroxy-benzoyl)piperazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under nitrogen atmosphere, 3,5-di-t-butyl-4-hydroxy-benzoic acid (3.10 g, 12.4 mmol.) and 1-benzylpiperazine (2.00 g, 11.3 mmol.) were dissolved in dichloromethane. Under chilling with ice, to this solution was portionwise added 1-(3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (2.87 g, 15.0 mmol.), and the resulting mixture was stirred overnight at room temperature. The reaction mixture was washed successively with saturated aqueous sodium hydrogen carbonate and water, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=20/1), to give the desired compound as an amorphous product (5.08 g, yield: 100%).

Workup

  1. temperatureUnder chilling with ice, to this solution
  2. washThe reaction mixture was washed successively with saturated aqueous sodium hydrogen carbonate and water
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (chloroform/methanol=20/1)

Sources & evidence

ORD record
ord-06a0725145a844dbb7713865c486204d
Source dataset
uspto-grants-2004_03
Patent number
US06706705B1

Linked notes

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