Water → 5-(N-benzoylamino)-2-phenyl-1,3,4,5-tetrahydrobenz[cd]indole

HRID 1637267Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1637267
[NH2:1][CH:2]1[C:12]2[C:13]3[C:5](=[C:6]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[NH:7][C:8]=3[CH:9]=[CH:10][CH:11]=2)[CH2:4][CH2:3]1.C(N(CC)CC)C.[C:27](Cl)(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.O>C(Cl)Cl>[C:27]([NH:1][CH:2]1[C:12]2[C:13]3[C:5](=[C:6]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[NH:7][C:8]=3[CH:9]=[CH:10][CH:11]=2)[CH2:4][CH2:3]1)(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 101988185-Amino-2-phenyl-1,3,4,5-tetrahydrobenz[cd]indole

Produkt 1

HCID 193482265-(N-benzoylamino)-2-phenyl-1,3,4,5-tetrahydrobenz[cd]indoleAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A portion (70 mg) of the compound obtained in Example 81 was dissolved in anhydrous methylene chloride (15 ml) and to the solution were added triethylamine (69 μl) and benzoyl chloride (29 μl). The mixture was stirred for 1 hour at room temperature. To the reaction mixture was added water, followed by extraction with methylene chloride. The organic layer was washed with 1N aqueous solution of sodium hydroxide, water and saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure to yield 90 mg (91%) of the titled compound.

Aufarbeitung

  1. extractionfollowed by extraction with methylene chloride
  2. washThe organic layer was washed with 1N aqueous solution of sodium hydroxide, water and saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThen, the solvent was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-e9305ab8d6404cc09a9368e43911d086
Quelldatensatz
uspto-grants-2000_03
Patentnummer
US06040331

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