Propargyl bromide → (2-Methoxyethyl)(methyl)(prop-2-yn-1-yl)amine

HRID 1266250Notes

Reaction equation

HRID 1266250 reaction equation
[CH2:1](Br)[C:2]#[CH:3].[CH3:5][O:6][CH2:7][CH2:8][NH:9][CH3:10].C(=O)([O-])[O-].[Cs+].[Cs+]>CC(C)=O>[CH3:5][O:6][CH2:7][CH2:8][N:9]([CH3:10])[CH2:1][C:2]#[CH:3]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 10796Cesium carbonateHCID 300977(2-Methoxyethyl)(methyl)amine

Product 1

HCID 18548974(2-Methoxyethyl)(methyl)(prop-2-yn-1-yl)amineYield 48.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Propargyl bromide (26.8 g, 225 mmol) was added dropwise to a mixture of N-(2-methoxyethyl)methyl amine (20 g, 225 mmol) and cesium carbonate (73 g, 225 mmol) in 350 mL of acetone. The mixture was stirred overnight under nitrogen at room temperature. The inorganic salts were then filtered off, and the solvent was removed. The residue was dissolved in saturated sodium bicarbonate solution and extracted with ethyl acetate. The organic extracts were then evaporated to give 14 g of (2-methoxy-ethyl)-methyl-prop-2-ynyl-amine: mass spectrum (m/e): M+H 127.

Workup

  1. filtrationThe inorganic salts were then filtered off
  2. customthe solvent was removed
  3. dissolutionThe residue was dissolved in saturated sodium bicarbonate solution
  4. extractionextracted with ethyl acetate
  5. customThe organic extracts were then evaporated

Sources & evidence

ORD record
ord-78bb8e842cfd4f54911eea255bf386dd
Source dataset
uspto-grants-2003_04
Patent number
US06548496B2

Reaction notes

Loading…