Ethylenediamine → 3-(2-Aminoethylamino)propane-1,2-diol

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Reaction Steps

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).

Provenance & Evidence