Reaction #985301

Reaction equation

Morpholine

potassium carbonate

propargyl bromide

→

colorless oil

Yield 70.0%

4-Prop-2-ynyl-morpholine

Yield 70.0%

Solvents

MeOH

Conditions

Workup

1. 1
   Temperaturecooled in ice under nitrogen
2. 2
   workup.STIRRINGStirring
3. 3
   Temperaturewithout cooling
4. 4
   FiltrationThe white suspension was filtered through paper
5. 5
   Washthe solids were washed with MeOH (100 ml)
6. 6
   Otherthe MeOH was carefully evaporated
7. 7
   Filtrationfiltered through paper
8. 8
   Othercarefully evaporated
9. 9
   workup.DISTILLATIONFinally the oil was distilled at 60° C./16 mbar

Procedure

Morpholine (100 ml, 1.148 mol) was dissolved in MeOH (1 L) and cooled in ice under nitrogen, then potassium carbonate (120 g, 0.63 mol) and propargyl bromide (124 mL, 1.148 mol) were added while stirring in ice. Stirring without cooling was continued for 4 h. The white suspension was filtered through paper and the solids were washed with MeOH (100 ml) and the MeOH was carefully evaporated. The white precipitate was suspended in DCM (400 ml), filtered through paper, and carefully evaporated. Finally the oil was distilled at 60° C./16 mbar. One obtained 100 g (70%) of a colorless oil.

Source