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

HRID 48925

Reaktionsgleichung

Reaktionsgleichung von HRID 48925
[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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-06a0725145a844dbb7713865c486204d
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06706705B1

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