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

HRID 426907Notes

Reaction equation

HRID 426907 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-075b73d460b34a8e875914f3ddda7237
Source dataset
uspto-grants-1979_10
Patent number
US04172094

Reaction notes

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