Reaction #1379897

Reaction equation

2-(2-aminoethylamino)ethanol

benzyl acrylate

→

2-(benzyloxycarbonylethyl]-2-(2aminoethylamino)ethanol

Conditions

Workup

1. 1
   Temperaturewas heated
2. 2
   Temperatureat reflux for 24 hours
3. 3
   OtherThe excess reagent was removed under reduced pressure
4. 4
   Otherthe resulting oil was purified by flash chromatography
5. 5
   workup.ADDITIONa mixture of dichloromethane and ethyl acetate (60:40)
6. 6
   Washto elute the desired material
7. 7
   OtherFractions were collected

Procedure

A solution of 2-(2-aminoethylamino)ethanol (4.6648 g; 44.8 mmole) dissolved in 35 mL of benzyl acrylate was heated at reflux for 24 hours. The excess reagent was removed under reduced pressure and the resulting oil was purified by flash chromatography using a mixture of dichloromethane and ethyl acetate (60:40) to elute the desired material. Fractions were collected and analyzed to determine which of these contain the product. Solvents were eliminated under vacuum to give 5.8 g (21.9%) of N,N,N′-tris[2-(benzyloxycarbonylethyl]-2-(2aminoethylamino)ethanol (8).

Source