4-(3,4-Dimethoxyphenyl)butyl azide → 4-(3,4-Dimethoxyphenyl)butan-1-amine

HRID 25105Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 25105
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][CH2:13][CH2:14][N:15]=[N+]=[N-])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[H-].[H-].[H-].[H-].[Li+].[Al+3]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][CH2:13][CH2:14][NH2:15])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Komponenten

3

Edukt 2

HCID 115867114-(3,4-Dimethoxyphenyl)butyl azideHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 116941674-(3,4-Dimethoxyphenyl)butan-1-amineAusbeute 42 %

Versuchsvorschrift

Amine 26 was prepared as described in procedure A from azide 25 (11.0 g, 49 mol) and LAH (26 mL of 1 M solution in THF). Crude 26 was purified by flash chromatography (silica gel, 93:7:1 chloroform/ethanol/concentrated ammonium hydroxide) to give pure 26 (4.8 g, 42%) as a clear oil. 1H NMR (300 MHz, CDCl3) δ1.42(m, 2H), 1.60 (m, 2H), 2.55 (m, 2H), 2.74 (m, 2H), 3.82 (s, 6H), 3.84 (s, 3H), 6.70 (m, 2H), 6.78 (m, 1H).

Aufarbeitung

  1. customAmine 26 was prepared
  2. customCrude 26 was purified by flash chromatography (silica gel, 93:7:1 chloroform/ethanol/concentrated ammonium hydroxide)

Quellen und Nachweise

ORD-Eintrag
ord-3fc29179a32148e2bf8949361fba1756
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06858614B2

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