4-(3,4-Dimethoxyphenyl)butyl azide → 3,4-Dimethoxybenzenebutanamine

HRID 25105Notes

Reaction equation

HRID 25105 reaction equation
[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]

Participants

3

Reactant 2

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

Product 1

HCID 116941673,4-DimethoxybenzenebutanamineYield 42%

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-3fc29179a32148e2bf8949361fba1756
Source dataset
uspto-grants-2005_02
Patent number
US06858614B2

Reaction notes

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