Reaction #415848

Reaction equation

potassium hydroxide

epichlorohydrin

epichlorohydrin

potassium chloride

Piperazine

→

N-GLYCIDYLPIPERAZINE

Solvents

ethanol

ethanol

Conditions

Workup

1. 1
   Otherequipped with a stirrer
2. 2
   Otherwas obtained
3. 3
   Temperaturewhile maintaining the temperature below 25° C.
4. 4
   Temperaturethe temperature was maintained below 25° C. for an additional 30 minutes
5. 5
   Temperaturewhile maintaining the temperature below 25° C
6. 6
   Otherhad formed during the reaction
7. 7
   Filtrationwas filtered from the mixture
8. 8
   Concentrationthe filtrate concentrated to one-half its volume
9. 9
   workup.ADDITIONOne liter of ethyl acetate was then added to the residual filtrate
10. 10
    OtherThe N-glycidylpiperazine oligomer precipitated as a white solid
11. 11
    FiltrationThe resultant slurry was filtered
12. 12
    workup.WAITafter standing several hours
13. 13
    OtherThe N-glycidylpiperazine oligomer collected on the
14. 14
    Filtrationfilter
15. 15
    Otherafter drying in vacuo at room temperature

Procedure

Piperazine (86.15 g., one mole) and ethanol (150 g.plus 1.5 g. water) were placed in a one liter 3-neck flask equipped with a stirrer, thermometer, dropping funnel and condenser. The mixture was stirred until a complete solution was obtained and then epichlorohydrin (92.53 g., one mole) was added dropwise while maintaining the temperature below 25° C., by means of an ice bath. After addition of the epichlorohydrin was complete, the temperature was maintained below 25° C. for an additional 30 minutes. Then a solution of 56.11 g. (1 mole) of potassium hydroxide in 225 g. of ethanol was added over a period 30 minutes while maintaining the temperature below 25° C. After cooling to 15° C. the potassium chloride which had formed during the reaction was filtered from the mixture and the filtrate concentrated to one-half its volume by stripping under vacuum. One liter of ethyl acetate was then added to the residual filtrate. The N-glycidylpiperazine oligomer precipitated as a white solid. The resultant slurry was filtered after standing several hours. The N-glycidylpiperazine oligomer collected on the filter after drying in vacuo at room temperature amounted to 119 grams, 83.8% of the theoretical yield. Elemental analysis indicated: %C, 56.09; %H, 9.55; %N, 18.55; %O, 15.77. The number average molecular weight as determined by vapor pressure osmometry was 705. This data corresponds to the formula: ##STR5##

Source