2-(4-Aminophenyl)ethylamine → HCID 21190160, Verbindung

HRID 619530

Reaktionsgleichung

Reaktionsgleichung von HRID 619530
Cl[C:2]1[N:7]2[C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:9]([CH3:11])[N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1.[NH2:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][NH2:26])=[CH:20][CH:19]=1.C(N(CC)C(C)C)(C)C>C(#N)C>[NH2:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][NH:26][C:2]2[N:7]3[C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:9]([CH3:11])[N:10]=[C:6]3[CH:5]=[CH:4][CH:3]=2)=[CH:20][CH:19]=1

Komponenten

5

Edukt 3

HCID 728952-(4-Aminophenyl)ethylamineHCID 81531DiisopropylethylamineHCID 2736382Ethyl 5-chloro-2-methylimidazo[1,2-a]pyridine-3-carboxylate

Produkt 1

HCID 21190160HCID 21190160, VerbindungAusbeute 75,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 4.07 g (17.1 mmol) of 5-chloro-3-ethoxycarbonyl-2-methylimidazo[1,2-a)pyridine, 3.48 g (25.6 mmol) of 2-(4-aminophenyl)ethylamine and 4.41 g (34.1 mmol) of N,N-diisopropylethylamine in 60 ml of acetonitrile was heated for 64 hours under reflux with stirring. After cooling, the solvent was distilled off. To the residue was added chloroform. The residue was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off. The residue was purified by column chromatography (eluent: chloroform/methanol=30:1) and recrystallized from ethyl acetate-n-hexane to give 4.37 g of the desired compound (75.7%, pale brown crystals).

Aufarbeitung

  1. temperaturewas heated for 64 hours
  2. temperatureunder reflux
  3. temperatureAfter cooling
  4. distillationthe solvent was distilled off
  5. additionTo the residue was added chloroform
  6. washThe residue was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe solvent was distilled off
  9. customThe residue was purified by column chromatography (eluent: chloroform/methanol=30:1)
  10. customrecrystallized from ethyl acetate-n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-824aa5e34e1840fab29a7b6aefcf2fcc
Quelldatensatz
uspto-grants-1999_09
Patentnummer
US05958942

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