Reaction #1211

Reaction equation

KOH

N2

N,N-bis(2-hydroxyethyl)-16-hydroxyhexadecanamide

LiAlH4

→

title compound

Yield 62.0%

16-[N,N-bis(2-hydroxyethyl)amino]-1-hexadecanol

Yield 62.0%

Solvents

tetrahydrofuran

Conditions

Workup

1. 1
   OtherA 500-ml flask equipped with a stirrer
2. 2
   Temperaturereflux condenser
3. 3
   workup.ADDITIONwere added
4. 4
   TemperatureAfter cooling the reaction mixture to room temperature
5. 5
   Othera salt deposited was separated by filtration
6. 6
   workup.DISTILLATIONThe solvent was then distilled off under reduced pressure
7. 7
   Otherthe resultant residue was purified by column chromatography on silica gel

Procedure

A 500-ml flask equipped with a stirrer and reflux condenser was charged with 3.01 g (79.3 mmol) of LiAlH4 and 200 ml of tetrahydrofuran. While stirring the mixture at room temperature in an N2 atmosphere, 5.00 g (13.9 mmol) of N,N-bis(2-hydroxyethyl)-16-hydroxyhexadecanamide were added, followed by stirring at 65° C. for 18 hours. After cooling the reaction mixture to room temperature, 15 g of 3% aqueous KOH were added, and a salt deposited was separated by filtration. The solvent was then distilled off under reduced pressure, and the resultant residue was purified by column chromatography on silica gel, thereby obtaining 2.98 g (yield: 62%) of the title compound (IId-3).

Source