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Piperazine → 2-(4-Bromophenyl)-2-isopropyl-5-(4-phenylpiperazine-1-yl)pentanoic acid methyl ester

HRID 547984
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 547984
[CH3:1][O:2][C:3](=[O:19])[C:4]([C:12]1[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][CH:13]=1)([CH:9]([CH3:11])[CH3:10])[CH2:5][CH2:6][CH2:7]Br.[C:20]1([N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.N1CCNCC1.CCN(CC)CC.I([O-])(=O)=O.[Na+]>C(#N)C>[CH3:1][O:2][C:3](=[O:19])[C:4]([C:12]1[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][CH:13]=1)([CH:9]([CH3:11])[CH3:10])[CH2:5][CH2:6][CH2:7][N:29]1[CH2:30][CH2:31][N:26]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:27][CH2:28]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 4837PiperazineHCID 70961-PhenylpiperazineHCID 8471TriethylamineHCID 23675764Sodium IodateHCID 468558605-Bromo-2-(4-bromophenyl)-2-isopropylpentanoic acid methyl ester

Produkt 1

HCID 461867402-(4-Bromophenyl)-2-isopropyl-5-(4-phenylpiperazine-1-yl)pentanoic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

After the 5-bromo-2-(4-bromophenyl)-2-isopropylpentanoic acid methyl ester (200 mg, 1 eq) was dissolved in acetonitrile, 4-phenylpiperazine (70 mg, 1 eq) as a piperazine derivative, Et3N (0.06 ml, 1.2 eq), and sodium iodate were added into the solution and heated and refluxed for 3 hours. When the reaction was completed, the precipitate was filtrated and the mixture was vacuum distilled and extracted with ethyl acetate and water. After the organic layer was washed with 1N HCl and saturated NaHCO3, the target compound 2-(4-bromophenyl)-2-isopropyl-5-(4-phenylpiperazine-1-yl)pentanoic acid methyl ester was obtained by drying the mixture with anhydrous sodium sulfate and removing the solvent at low pressures (69 mg, 42%).

Aufarbeitung

  1. temperatureheated
  2. temperaturerefluxed for 3 hours
  3. filtrationthe precipitate was filtrated
  4. distillationdistilled
  5. extractionextracted with ethyl acetate and water
  6. washAfter the organic layer was washed with 1N HCl and saturated NaHCO3

Quellen und Nachweise

ORD-Eintrag
ord-5be30e553d664163ac3b72e36c175460
Quelldatensatz
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07939672B2

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