Propargyl bromide → 4-(2-Propyn-1-yl)morpholine

HRID 898119Notes

Reaction equation

HRID 898119 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[CH2:13](Br)[C:14]#[CH:15]>CO>[CH2:15]([N:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1)[C:14]#[CH:13]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 8083MorpholineHCID 11430Potassium Carbonate

Product 1

HCID 4129414-(2-Propyn-1-yl)morpholineYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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.

Workup

  1. temperaturecooled in ice under nitrogen
  2. stirringStirring
  3. temperaturewithout cooling
  4. filtrationThe white suspension was filtered through paper
  5. washthe solids were washed with MeOH (100 ml)
  6. customthe MeOH was carefully evaporated
  7. filtrationfiltered through paper
  8. customcarefully evaporated
  9. distillationFinally the oil was distilled at 60° C./16 mbar

Sources & evidence

ORD record
ord-dfb84e9f027540deb9d37feb2d5b8c9a
Source dataset
uspto-grants-2008_04
Patent number
US07351700B2

Reaction notes

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