Propargyl bromide → 1-Ethyl-4-(prop-2-ynyl)piperazine

HRID 1068979Notes

Reaction equation

HRID 1068979 reaction equation
[CH2:1](Br)[C:2]#[CH:3].[CH2:5]([N:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1)[CH3:6].C(=O)([O-])[O-].[Cs+].[Cs+]>CC(C)=O>[CH2:5]([N:7]1[CH2:12][CH2:11][N:10]([CH2:1][C:2]#[CH:3])[CH2:9][CH2:8]1)[CH3:6]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 10796Cesium carbonateHCID 791961-Ethylpiperazine

Product 1

HCID 211907411-Ethyl-4-(prop-2-ynyl)piperazineYield 71.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Propargyl bromide (20.8 g, 175 mmol) was added dropwise to a mixture of 1-ethyl piperazine (20 g, 175 mmol) and cesium carbonate (57 g, 175 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 19 g of 1-ethyl-4-prop-2-ynyl-piperazine: mass spectrum (m/e): M+H 153.

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-151a1afaf95d4694adc3c00d359b38d0
Source dataset
uspto-grants-2001_06
Patent number
US06251912B1

Reaction notes

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