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Sodium Hydroxide → Tert-butyl 4-[4-(4-amino-1,2,5-oxadiazol-3-yl)phenyl]piperazine-1-carboxylate

HRID 1744121
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1744121
[C:1](/[C:3](=[N:23]\[OH:24])/[C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)#[N:2].Cl.[NH2:26]O.C([O-])(O)=O.[Na+].[OH-].[Na+]>CCO.O.[Cl-].[Na+].O>[NH2:2][C:1]1[C:3]([C:4]2[CH:5]=[CH:6][C:7]([N:10]3[CH2:11][CH2:12][N:13]([C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[CH2:14][CH2:15]3)=[CH:8][CH:9]=2)=[N:23][O:24][N:26]=1
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Komponenten

8

Edukt 4

HCID 14798Sodium Hydroxide2×HCID 443297Hydroxyamine hydrochloride2×HCID 516892Sodium Bicarbonate2×HCID 22236172tert-butyl 4-[4-[(Z)-C-cyano-N-hydroxycarbonimidoyl]phenyl]piperazine-1-carboxylate

Produkt 1

HCID 22235822Tert-butyl 4-[4-(4-amino-1,2,5-oxadiazol-3-yl)phenyl]piperazine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel2×HCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

To tert-butyl 4-{4-[(Z)-cyano(hydroxyimino)methyl]phenyl}piperazine-1-carboxylate (1.39 g, 4.21 mmol) in EtOH (50 mL) was added an aqueous solution of pre-mixed hydroxylamine hydrochloride (440 mg, 6.32 mmol) and NaHCO3 (535 mg, 6.32 mmol) in water (15 mL) and the reaction was refluxed overnight. An additional aliquot of hydroxylamine hydrochloride (440 mg, 6.32 mmol) and NaHCO3 (535 mg, 6.32 mmol) in water (10 mL) was added and the reaction was refluxed for 2 hours. Aqueous NaOH (1.0 M, 42.1 mL) was added and the reaction was refluxed for 1 hour. An additional aliquot of NaOH (1.0 M, 21 mL) was added and the reaction was refluxed for 3 hours. After cooling to rt, the reaction mixture was poured into brine and the product extracted with EtOAc (2×), dried over Na2SO4, concentrated in vacuo, and purified by flash chromatography over silica gel (EtOAc/Hex, 4/6) to afford tert-butyl 4-[4-(4-amino-1,2,5-oxadiazol-3-yl)phenyl]piperazine-1-carboxylate.

Aufarbeitung

  1. temperaturethe reaction was refluxed overnight
  2. temperaturethe reaction was refluxed for 2 hours
  3. temperaturethe reaction was refluxed for 1 hour
  4. temperaturethe reaction was refluxed for 3 hours
  5. extractionthe product extracted with EtOAc (2×)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. custompurified by flash chromatography over silica gel (EtOAc/Hex, 4/6)

Quellen und Nachweise

ORD-Eintrag
ord-e7db718def9e4c408bcf41be36ee34f1
Quelldatensatz
uspto-grants-2006_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07012075B2

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