Aluminium lithium hydride → 4-(2,4-Dimethoxyphenyl)butan-1-amine

HRID 25111Notes

Reaction equation

HRID 25111 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[CH2:11][CH2:12][CH2:13][CH2:14][N:15]=[N+]=[N-].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[CH2:11][CH2:12][CH2:13][CH2:14][NH2:15]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 225661244-(2,4-Dimethoxyphenyl)butyl azide

Product 1

HCID 225661354-(2,4-Dimethoxyphenyl)butan-1-amineYield 64.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Amine 79 was prepared by typical procedure A from azide 78 (4.06 g, 0.017 mol) and LiAlH4 (13 mL of a 1.0 M solution in THF). The material was purified by column chromatography (silica gel, 2:1:0.1 chloroform/ethanol/concentrated ammonium hydroxide) to provide 79 (2.3 g, 64%) as a white solid. 1H NMR (300 MHz, CDCl3) δ1.53 (m, 4H), 2.53 (m, 2H), 2.73 (m, 2H), 3.80 (s, 6H), 6.43 (m, 2H), 7.52 (m, 1H).

Workup

  1. customThe material was purified by column chromatography (silica gel, 2:1:0.1 chloroform/ethanol/concentrated ammonium hydroxide)

Sources & evidence

ORD record
ord-3ac148f607d945d0a278ca4f83dfcb6d
Source dataset
uspto-grants-2005_02
Patent number
US06858614B2

Reaction notes

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