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

HRID 241830Notes

Reaction equation

HRID 241830 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1)[CH3:2].C([O-])([O-])=O.[K+].[K+].[CH2:15](Br)[C:16]#[CH:17]>CC(C)=O>[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([CH2:17][C:16]#[CH:15])[CH2:5][CH2:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 791961-Ethylpiperazine

Product 1

HCID 211907411-Ethyl-4-(prop-2-ynyl)piperazine

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To the 1-ethylpiperazine (2.33 g, 20.2 mmol) and K2CO3 (2.79 g, 20.2 mmol) in acetone (27 ml) was added propargyl bromide (2.00 g, 13.5 mmol) dropwise at 0° C. under N2. The reaction was stirred at room temperature overnight. The reaction was filtered and the salts washed with a small amount of acetone. The filtrates were combined and evaporated gently to concentration. The residue was taken up in EtOAc and washed with water. The aqueous phase was re-extracted with EtOAc. The combined organic layers were washed with brine and dried over MgSO4. The product was filtered and evaporated to dryness to leave a pale orange oil.

Workup

  1. filtrationThe reaction was filtered
  2. washthe salts washed with a small amount of acetone
  3. customevaporated gently to concentration
  4. washwashed with water
  5. extractionThe aqueous phase was re-extracted with EtOAc
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationThe product was filtered
  9. customevaporated to dryness
  10. customto leave a pale orange oil

Sources & evidence

ORD record
ord-73cdd00e5afc4df8bb19372bffddee08
Source dataset
uspto-grants-2014_02
Patent number
US08653084B2

Reaction notes

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