Ethylenediamine → 1,2-Propanediol, 3-((2-aminoethyl)amino)-

HRID 1613020Notes

Reaction equation

HRID 1613020 reaction equation
Cl[CH2:2][CH:3]([OH:6])[CH2:4][OH:5].[CH2:7]([NH2:10])[CH2:8][NH2:9].[OH-].[Na+]>>[OH:6][CH:3]([CH2:4][OH:5])[CH2:2][NH:9][CH2:8][CH2:7][NH2:10]

Participants

4

Reactant 3

HCID 3301Ethylenediamine2×HCID 72903-Chloro-1,2-propanediol2×HCID 14798Sodium Hydroxide

Product 1

HCID 3344021,2-Propanediol, 3-((2-aminoethyl)amino)-Yield 43%

Procedure

Following the procedure of Surrey et al., J. Am. Chem. Soc. (1952) 74:4102, 3-chloro-1,2-propanediol (8.36 ml, 0.10 mole) was added dropwise over 15 min to stirring ethylenediamine (66.8 ml, 1.0 mole) at room temperature. After the addition was complete, the solution was heated at approx. 60° C. until the 3-chloro-1,2-propanediol was consumed (about 1 hour), as determined by TLC. NaOH (4.4 g, 0.11 mole) was added to the solution and excess ethylenediamine was vacuum distilled off followed by careful fractional distillation to yield 5.76 g (43%) of (36) (b.p. 162° C./2.0 mm).

Workup

  1. additionAfter the addition
  2. customwas consumed (about 1 hour)
  3. distillationdistilled off
  4. distillationfollowed by careful fractional distillation

Sources & evidence

ORD record
ord-2b029b987cb845c092ebba30c789766a
Source dataset
uspto-grants-1993_03
Patent number
US05191119

Reaction notes

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