1-Ethyl-4-(3,4,5-trimethoxyphenyl)-1-(2-thienyl)butyl isocyanide → 1-ethyl-4-(3,4,5-trimethoxyphenyl)-1-(2-thienyl)-N-methylbutylamine
Reaction equation
[CH2:1]([C:3]([N+:24]#[C-:25])([C:19]1[S:20][CH:21]=[CH:22][CH:23]=1)[CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([O:15][CH3:16])=[C:9]([O:17][CH3:18])[CH:8]=1)[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH2:1]([C:3]([NH:24][CH3:25])([C:19]1[S:20][CH:21]=[CH:22][CH:23]=1)[CH2:4][CH2:5][CH2:6][C:7]1[CH:8]=[C:9]([O:17][CH3:18])[C:10]([O:15][CH3:16])=[C:11]([O:13][CH3:14])[CH:12]=1)[CH3:2]Participants
4
Procedure
A solution of 2.8 g of 1-ethyl-4-(3,4,5-trimethoxyphenyl)-1-(2-thienyl)butyl isocyanide in 10 ml of tetrahydrofuran is added dropwise to a suspension of 0.6 g of lithium aluminum hydride in 5 ml of tetrahydrofuran under ice-cooling and the mixture is stirred at room temperature for 16 hours. To the reaction mixture are added successively, 0.6 ml of water, 0.6 ml of an aqueous 15% sodium hydroxide solution and 1.8 ml of water, and the insoluble materials are removed by filtration. The filtrate is concentrated under reduced pressure and the residue is purified by silica gel column chromatography (solvent; chloroform:ethanol=20:1) to give 1.7 g of 1-ethyl-4-(3,4,5-trimethoxyphenyl)-1-(2-thienyl)-N-methylbutylamine as a colorless oil. yield:60%