Propargyl bromide → 2-Propyn-1-amine, N,N-bis(1-methylethyl)-

HRID 1068993Notes

Reaction equation

HRID 1068993 reaction equation
[CH2:1](Br)[C:2]#[CH:3].[CH:5]([NH:8][CH:9]([CH3:11])[CH3:10])([CH3:7])[CH3:6].C(=O)([O-])[O-].[Cs+].[Cs+]>CC(C)=O>[CH:5]([N:8]([CH:9]([CH3:11])[CH3:10])[CH2:3][C:2]#[CH:1])([CH3:7])[CH3:6]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 7912DiisopropylamineHCID 10796Cesium carbonate

Product 1

HCID 2343732-Propyn-1-amine, N,N-bis(1-methylethyl)-Yield 43.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Propargyl bromide (23.5 g, 197 mmol) was added dropwise to a mixture of diisopropyl amine (20 g, 197 mmol) and cesium carbonate (64 g, 197 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 12 g of diisopropyl-prop-2-ynyl-amine: mass spectrum (m/e): M+H 139.

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-04a454394aee4c8cb564afe2bbf69364
Source dataset
uspto-grants-2001_06
Patent number
US06251912B1

Reaction notes

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