Propargyl bromide → 1-Methyl-4-(prop-2-yn-1-yl)piperazine

HRID 1266248Notes

Reaction equation

HRID 1266248 reaction equation
[CH2:1](Br)[C:2]#[CH:3].[CH3:5][N:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CC(C)=O>[CH3:5][N:6]1[CH2:11][CH2:10][N:9]([CH2:1][C:2]#[CH:3])[CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 10796Cesium carbonateHCID 531671-Methylpiperazine

Product 1

HCID 135140911-Methyl-4-(prop-2-yn-1-yl)piperazineYield 27.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Propargyl bromide (23.8 g, 200 mmol) was added dropwise to a mixture of 1-methyl-piperazine (20 g, 200 mmol) and cesium carbonate (65 g, 200 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 7.5 g of 1-methyl-4-prop-2-ynyl-piperazine: 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-cabda2b85ea04f5d91d204e78a862607
Source dataset
uspto-grants-2003_04
Patent number
US06548496B2

Reaction notes

Loading…