Cycloheptylamine → N-Cycloheptyl-[(2-phenanthrenyl)methyl]amine

HRID 37640

Reaktionsgleichung

Reaktionsgleichung von HRID 37640
[CH3:1][C:2]1[CH:15]=[CH:14][C:13]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH:6]=[CH:5][C:4]=2[CH:3]=1.BrN1C(=O)CCC1=O.[CH:24]1([NH2:31])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH:24]1([NH:31][CH2:1][C:2]2[CH:15]=[CH:14][C:13]3[C:12]4[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=4)[CH:6]=[CH:5][C:4]=3[CH:3]=2)[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

Komponenten

6

Edukt 4

HCID 2899CycloheptylamineHCID 11430Potassium CarbonateHCID 173212-MethylphenanthreneHCID 67184N-bromobutanimide

Produkt 1

HCID 15284290N-Cycloheptyl-[(2-phenanthrenyl)methyl]amineAusbeute 66,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2-Methylphenanthrene (2.00 g, 10.4 mmol) was brominated with N-bromosuccinimide (2.05 g, 11.5 mmol) and the product compound was added gradually to a suspension of cycloheptylamine (2.38 g, 21.0 mmol) and potassium carbonate (2.90 μg, 21.0 mmol) in dimethylformamide (20 ml) with ice-cooling. The mixture was then stirred at room temperature for 16 hrs and, then, filtered and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give 2.11 g of a viscous liquid. 1H-NMR (δ ppm, in deuteriochloroform) 2.83 (2H, m), 4.02 (2H, s), 8.68 (2H, m)

Aufarbeitung

  1. temperaturecooling
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b2325b9e98944fdc89b7e22fd4005c14
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05420348

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