Reaction #1215

Reaction equation

ethyl 12-hydroxystearate

aminoethylaminoethanol

sodium methoxide

N2

→

title compound

N-[2-(2-hydroxyethylamino)ethyl]-12-hydroxyoctadecanamide

Solvents

water

THF

Conditions

Workup

1. 1
   OtherA 30-ml two-necked flask equipped with a stirrer
2. 2
   TemperatureWhile heating
3. 3
   OtherAfter completion of the reaction
4. 4
   Otherformed
5. 5
   Otherwas purified by flash column chromatography on silica gel

Procedure

A 30-ml two-necked flask equipped with a stirrer and dropping funnel was charged with 2.08 g (20 mmol) of aminoethylaminoethanol and 0.054 g (1 mmol) of sodium methoxide. While heating and stirring the contents at 80° C. in an N2 atmosphere, a solution of 3.29 g (10 mmol) of ethyl 12-hydroxystearate in 10 ml of THF was added dropwise over 2 hours. The resultant mixture was stirred further for 13 hours at 80° C. under reduced pressure. After completion of the reaction, the reaction mixture was poured into 500 ml of water, and precipitate formed was purified by flash column chromatography on silica gel, thereby obtaining 2.85 g (yield: 74%) of the title compound (IIf-1).

Source