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1-(4-Nitrophenyl)piperazine → HCID 18403833, Verbindung

HRID 1017685
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1017685
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][C:12]([NH:14][CH3:15])=[O:13])[CH:6]=O.[N+:16]([C:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[CH:21][CH:20]=1)([O-:18])=[O:17].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:6][N:28]2[CH2:29][CH2:30][N:25]([C:22]3[CH:21]=[CH:20][C:19]([N+:16]([O-:18])=[O:17])=[CH:24][CH:23]=3)[CH2:26][CH2:27]2)[CH:8]=[CH:9][C:10]=1[O:11][C:12]([NH:14][CH3:15])=[O:13]
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Komponenten

5

Edukt 3

HCID 804471-(4-Nitrophenyl)piperazineHCID 4064704HCID 4064704, VerbindungHCID 5049666Sodium triacetoxyborohydride

Produkt 1

HCID 18403833HCID 18403833, VerbindungAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

To a solution of 3-methoxy-4-(methylaminocarbonyloxy)benzaldehyde (1.01 g) in 1,2-dichloroethane (19.0 ml) was added 1-(4-nitrophenyl)piperazine (1.0 g), and sodium triacetoxyborohydride (1.54 g), with stirring. The reaction mixture was stirred for 3 hrs at ambient temperature, poured into ice/saturated sodium carbonate solution (100 ml) and extracted with dichloromethane. The combined organic extracts were washed with water and brine, dried over sodium sulfate, filtered, and the filtrate was concentrated. The residue was flash chromatographed (silica gel), eluting with dichloromethane, followed by 1% methanol:dichloromethane. The appropriate fractions were collected and concentrated to give 1.66 g (86%) of product. Recrystallization from ethyl acetate gave the analytical sample, mp 155-157° C.

Aufarbeitung

  1. stirringThe reaction mixture was stirred for 3 hrs at ambient temperature
  2. extractionextracted with dichloromethane
  3. washThe combined organic extracts were washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customchromatographed (silica gel)
  8. washeluting with dichloromethane
  9. customThe appropriate fractions were collected
  10. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-426a0a58db0645b7aeb460946f838425
Quelldatensatz
uspto-grants-2002_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06479495B1

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