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

HRID 462324Notes

Reaction equation

HRID 462324 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-9575930fa8e349bf8a118a17d4b7a1c2
Source dataset
uspto-grants-1977_12
Patent number
US04065497

Reaction notes

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