Glycidol → N,N,N'-Tri-(2,3-dihydroxypropyl)trimethylenediamine

HRID 443526Notes

Reaction equation

HRID 443526 reaction equation
[OH:1][CH:2]([CH2:14][OH:15])[CH2:3][N:4]([CH2:9][CH:10]([OH:13])[CH2:11][OH:12])[CH2:5][CH2:6][CH2:7][NH2:8].[CH2:16]1[O:18][CH:17]1[CH2:19][OH:20]>CO>[OH:1][CH:2]([CH2:14][OH:15])[CH2:3][N:4]([CH2:9][CH:10]([OH:13])[CH2:11][OH:12])[CH2:5][CH2:6][CH2:7][NH:8][CH2:16][CH:17]([OH:18])[CH2:19][OH:20]

Participants

4

Reactant 2

HCID 11164GlycidolHCID 234677983,3'-[(3-Aminopropyl)azanediyl]di(propane-1,2-diol)

Product 1

HCID 23467815N,N,N'-Tri-(2,3-dihydroxypropyl)trimethylenediamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N,N-di-(2,3-dihydroxypropyl)trimethylenediamine (11.1 g., 0.05 mole) is dissolved in 125 ml. of methanol and heated under reflux with agitation. Glycidol (3.7 g., 0.05 mole) is added dropwise over a period of 1.5 hour and the solution mixed an additional hour at 60° C.-80° C. The methyl alcohol and other volatiles are removed by stripping under reduced pressure to leave the product suitable for use in the next steps.

Workup

  1. temperatureunder reflux with agitation
  2. additionthe solution mixed an additional hour at 60° C.-80° C
  3. customThe methyl alcohol and other volatiles are removed
  4. customto leave the product suitable for use in the next steps

Sources & evidence

ORD record
ord-5b08ab0df8f54ff0a4a116a1f9eb8f66
Source dataset
uspto-grants-1981_04
Patent number
US04260760

Reaction notes

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