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

HRID 458606Notes

Reaction equation

HRID 458606 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) δ 1.42(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-bc72a34b56f444cd86229f6b748e6a1f
Source dataset
uspto-grants-2007_03
Patent number
US07192959B2

Reaction notes

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