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

HRID 506997Notes

Reaction equation

HRID 506997 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[NH:7]1[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1.[CH2:13](Br)[C:14]#[CH:15]>CC(C)=O>[N:7]1([CH2:15][C:14]#[CH:13])[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 8083MorpholineHCID 10796Cesium carbonate

Product 1

HCID 4129414-(2-Propyn-1-yl)morpholine

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of cesium carbonate (1.6 g) and morpholine (0.437 ml) in acetone (10 ml) was added propargyl bromide (557 μl of 80% wt. in toluene) dropwise. The mixture was stirred at room temperature for 18 hours. The insoluble material was removed by filtration and the filtrate concentrated. The residue dissolved in ethyl acetate, washed with saturated NaHCO3 solution, dried (magnesium sulfate) and concentrated to yield 3-(4-morpholinyl)-1-propyne as a brown oil (494 mg); NMR Spectrum: (DMSOd6) 2.19 (t, 1H), 2.50 (m, 4H), 3.22 (d, 2H), 3.67 m, 4H).

Workup

  1. customThe insoluble material was removed by filtration
  2. concentrationthe filtrate concentrated
  3. dissolutionThe residue dissolved in ethyl acetate
  4. washwashed with saturated NaHCO3 solution
  5. dry with materialdried (magnesium sulfate)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b91129823e92490b8cdc6e20592a60fd
Source dataset
uspto-grants-2010_08
Patent number
US07786115B2

Reaction notes

Loading…