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

HRID 1266246Notes

Reaction equation

HRID 1266246 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-2a2c6e7954d04bcd8d265059000432b5
Source dataset
uspto-grants-2003_04
Patent number
US06548496B2

Reaction notes

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