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

HRID 866712Notes

Reaction equation

HRID 866712 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) was dissolved in 125 ml. of methanol and heated under reflux with agitation. Glycidol (3.7 g., 0.05 mole) was 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 were 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 were removed
  4. customto leave the product suitable for use in the next steps

Sources & evidence

ORD record
ord-6f1bab27df584a218d961242f9fa18ce
Source dataset
uspto-grants-1978_07
Patent number
US04100193

Reaction notes

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