1-Ethyl-4-(3,4,5-trimethoxyphenyl)-1-(2-thienyl)butyl isocyanide → 1-ethyl-4-(3,4,5-trimethoxyphenyl)-1-(2-thienyl)-N-methylbutylamine

HRID 1708966Notes

Reaction equation

HRID 1708966 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

Reactant 2

HCID 108323281-Ethyl-4-(3,4,5-trimethoxyphenyl)-1-(2-thienyl)butyl isocyanideHCID 21226445Aluminium lithium hydride

Product 1

HCID 106424791-ethyl-4-(3,4,5-trimethoxyphenyl)-1-(2-thienyl)-N-methylbutylamineYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

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%

Workup

  1. temperaturecooling
  2. additionTo the reaction mixture are added successively
  3. custom0.6 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
  4. concentrationThe filtrate is concentrated under reduced pressure
  5. customthe residue is purified by silica gel column chromatography (solvent; chloroform:ethanol=20:1)

Sources & evidence

ORD record
ord-188b9ccbbbb0424289b6848952e98066
Source dataset
uspto-grants-1990_08
Patent number
US04946862

Reaction notes

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