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

HRID 1296461Notes

Reaction equation

HRID 1296461 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) δ 1.53 (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-39de6d200a6d48bfbfe70d2ca2f844b2
Source dataset
uspto-grants-2007_07
Patent number
US07247636B2

Reaction notes

Loading…