Hexamethylenediamine → N~1~,N~2~,N~4~-Tris(6-aminohexyl)aspartamide

HRID 845139Notes

Reaction equation

HRID 845139 reaction equation
[C:1]([O:9]C)(=O)/[CH:2]=[CH:3]\[C:4](OC)=[O:5].[CH2:11]([NH2:18])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][NH2:17]>C1(C)C=CC=CC=1>[NH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][NH:18][C:1](=[O:9])[CH:2]([NH:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][NH2:18])[CH2:3][C:4]([NH:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][NH2:18])=[O:5]

Participants

4

Reactant 2

HCID 16402HexamethylenediamineHCID 5271565Dimethyl maleate

Product 1

HCID 19920859N~1~,N~2~,N~4~-Tris(6-aminohexyl)aspartamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Dimethyl maleate (72 g, 0.5 moles) is added over a 2-3 hour period to a solution of 1,6-hexanediamine (174 g, 1.5 moles) in toluene (360 g) at 75°-80° C. The reaction temperature rises from 80° to 110° C. under reflux conditions. After the addition is completed, methanol is distilled at a reaction temperature of 120°-125° C. Additional toluene (320 g) is added to maintain reaction volume. The reaction may be followed by amine titration or by disappearance of the methyl ester in the 1H NMR spectrum. After the reaction is complete, toluene is removed under vacuum (50°-70° C., 15-20 mm Hg) to give N,N'-bis(6-aminohexyl)-2-[(6-aminohexyl)amino]butanediamide as a viscous liquid which solidifies on standing.

Workup

  1. customrises from 80° to 110° C. under reflux conditions
  2. additionAfter the addition
  3. distillationmethanol is distilled at a reaction temperature of 120°-125° C
  4. additionAdditional toluene (320 g) is added
  5. temperatureto maintain
  6. customreaction volume
  7. customThe reaction
  8. customtoluene is removed under vacuum (50°-70° C., 15-20 mm Hg)

Sources & evidence

ORD record
ord-b2ecd6362bbf445e9a59d6972112ecb6
Source dataset
uspto-grants-1988_07
Patent number
US04755623

Reaction notes

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