Water → 1,3-Propanediamine, N-[2-(3,4-dimethoxyphenyl)ethyl]-N-methyl-

HRID 1601337Notes

Reaction equation

HRID 1601337 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][N:13]([CH3:19])[CH2:14][CH2:15][C:16]([NH2:18])=O)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1.C(OCC)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][N:13]([CH3:19])[CH2:14][CH2:15][CH2:16][NH2:18])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 205912053-[[2-(3,4-Dimethoxyphenyl)ethyl]methylamino]propanamideHCID 21226445Aluminium lithium hydride

Product 1

HCID 104449491,3-Propanediamine, N-[2-(3,4-dimethoxyphenyl)ethyl]-N-methyl-Yield 60.9%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.5 g (5.6 mmol) 3-[[2-(3,4-Dimethoxyphenyl)ethyl]methylamino]propanamide (D1) in dry tetrahydrofuran were added dropwise to a suspension of 0.64 g (1.7 mmol) lithium aluminium hydride in 20 ml dry diethylether whilst stirring. The mixture was heated under reflux for 2 hours then cooled with a bath of ice water before carefully adding dropwise 0.65 ml water, 0.65 ml 15% aqueous NaOH, then 1.95 ml water. The mixture was dried over MgSO4, concentrated in vacuo and the residue was purified twice by chromatography on basic alumina using methylene chloride/methanol: 95/5 then methylene chloride/methanol/30% aqueous ammonia: 90/10/0.1 to yield 0.86 g (60.8%) of the desired compound.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. dry with materialThe mixture was dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customthe residue was purified twice by chromatography on basic alumina

Sources & evidence

ORD record
ord-a72d6a29926d461b92bf7576fa3a0836
Source dataset
uspto-grants-1999_11
Patent number
US05977179

Reaction notes

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