Benzaldehyde → N-benzyl-N-[2-(9H-carbazol-2-yloxy)]ethylamine

HRID 2299561Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2299561
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:9]1[C:21]2[NH:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]=2[CH:12]=[CH:11][C:10]=1[O:22][CH2:23][CH2:24][NH2:25]>CO.[Pt]=O>[CH2:1]([NH:25][CH2:24][CH2:23][O:22][C:10]1[CH:11]=[CH:12][C:13]2[C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[NH:20][C:21]=2[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 2

HCID 240Benzaldehyde2×HCID 110854932-(9H-carbazol-2-yloxy)ethylamine

Produkt 1

HCID 11267065N-benzyl-N-[2-(9H-carbazol-2-yloxy)]ethylamine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 82844Platinum oxide (PtO)KatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

Benzaldehyde (9.38 g) was added to a solution of N-[2-(9H-carbazol-2-yloxy)]ethylamine (20 g; synthesized according to the process indicated in JP-A-9-249623) in methanol (500 mL). The mixture was then stirred at room temperature for 1 hour. Under an argon atmosphere, platinum oxide (1.00 g; mfd. by Wako Pure Chemical Industries) was added to the mixture, which was then stirred under a hydrogen atmosphere at atmospheric pressure for 3 hours. After replacing the atmosphere in the reaction system with argon, benzaldehyde (1.88 g) was added to the mixture, which was then further stirred under a hydrogen atmosphere at atmospheric pressure for 3 hours. After replacing the atmosphere with argon, the catalyst was filtered off and the solvent was distilled off under reduced pressure. The residue was recrystallized from ethanol and dried under reduced pressure to give the title compound (25.2 g) as a pale yellow crystal.

Aufarbeitung

  1. customsynthesized
  2. stirringwas then stirred under a hydrogen atmosphere at atmospheric pressure for 3 hours
  3. additionwas added to the mixture, which
  4. stirringwas then further stirred under a hydrogen atmosphere at atmospheric pressure for 3 hours
  5. filtrationthe catalyst was filtered off
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was recrystallized from ethanol
  8. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-84ede2cca9b7401c9fd33d743064dcf9
Quelldatensatz
uspto-grants-2002_12
Patentnummer
US06495701B1

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