Bis(2-Methoxyethyl)amine → N,N-Bis(2-methoxyethyl)-2-propyn-1-amine

HRID 276820Notes

Reaction equation

HRID 276820 reaction equation
[CH2:1](Br)[C:2]#[CH:3].[CH3:5][O:6][CH2:7][CH2:8][NH:9][CH2:10][CH2:11][O:12][CH3:13].C(=O)([O-])[O-].[Cs+].[Cs+]>CC(C)=O>[CH3:5][O:6][CH2:7][CH2:8][N:9]([CH2:10][CH2:11][O:12][CH3:13])[CH2:1][C:2]#[CH:3]

Participants

5

Reactant 3

HCID 2383Bis(2-Methoxyethyl)amineHCID 7842Propargyl bromideHCID 10796Cesium carbonate

Product 1

HCID 18548955N,N-Bis(2-methoxyethyl)-2-propyn-1-amineYield 77.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Propargyl bromide (17.8 g, 150 mmol) was added dropwise to a mixture of bis(2-methoxyethyl)amine (20 g, 150 mmol) and cesium carbonate (49 g, 150 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 20 g of bis-(2-methoxy-ethyl)-prop-2-ynyl-amine: mass spectrum (m/e): M+H 172.

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-c1e80942b4624903bc94ff78edb4b841
Source dataset
uspto-grants-2002_03
Patent number
US06355636B1

Reaction notes

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