Ethyl Bromide → 9-((N-(5-hydroxypentyl)-N-(ethyl)amino)methyl)anthracene

HRID 392995

Reaktionsgleichung

Reaktionsgleichung von HRID 392995
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][NH:7][CH2:8][C:9]1[C:10]2[C:15]([CH:16]=[C:17]3[C:22]=1[CH:21]=[CH:20][CH:19]=[CH:18]3)=[CH:14][CH:13]=[CH:12][CH:11]=2.C([O-])([O-])=O.[K+].[K+].[CH2:29](Br)[CH3:30]>C(#N)C>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][N:7]([CH2:8][C:9]1[C:10]2[C:15]([CH:16]=[C:17]3[C:22]=1[CH:21]=[CH:20][CH:19]=[CH:18]3)=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:29][CH3:30]

Komponenten

5

Edukt 3

HCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 108809079-((5-Hydroxypentyl)aminomethyl)anthracene

Produkt 1

HCID 226622019-((N-(5-hydroxypentyl)-N-(ethyl)amino)methyl)anthraceneAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

9-((5-hydroxypentyl)aminomethyl)anthracene (1.00 g, 3.41 mol) and K2CO3 (0.518 g, 3.75 mmol) were taken up in 25 mL acetonitrile. Ethyl bromide (11.14 g, 102 mmol) was added and the mixture was refluxed under nitrogen for 24 h. The mixture was filtered on a sintered-glass frit and the solvent and excess ethyl bromide was removed under reduced pressure. Removal of the solvent afforded 1.07 g (98% yield) of 6 as a yellow solid; 1H NMR (300.13 MHz, CD3CN) δ 1.15 (m, 2H), 1.38 (m, 5H), 1.81 (m, 2H), 3.05 (m, 4H), 3.49 (t, 2H), 5.21 (s, 2H), 7.45 (m, 2H), 7.62 (m, 2H), 8.05 (d, 2H), 8.44 (m, 3H); 13C—{1H} NMR (75.4 MHz, CDCl3) δ 131.8, 131.3, 130.8, 129.6, 128.0, 125.6, 124.0, 61.7, 53.1, 49.4, 48.7, 31.4, 23.9, 23.3, 10.0.

Aufarbeitung

  1. temperaturethe mixture was refluxed under nitrogen for 24 h
  2. filtrationThe mixture was filtered on a sintered-glass frit
  3. customthe solvent and excess ethyl bromide was removed under reduced pressure
  4. customRemoval of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-df8cbe3b5b034d34b7cfd70dd83e4e99
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06804544B2

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