Piperazine → 1-(But-3-yn-1-yl)piperazine

HRID 417876Notes

Reaction equation

HRID 417876 reaction equation
CC1C=CC(S(O[CH2:12][CH2:13][C:14]#[CH:15])(=O)=O)=CC=1.[NH:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1>CCO>[CH2:12]([N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)[CH2:13][C:14]#[CH:15]

Participants

4

Reactant 2

HCID 4837PiperazineHCID 2720203-Butynyl p-toluenesulfonate

Product 1

HCID 247002581-(But-3-yn-1-yl)piperazine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of but-3-ynyl 4-methylbenzenesulfonate (2.0 mL) and piperazine (2.0 g) in EtOH (6 mL) was heated to reflux for 30 min. The mixture was concentrated, diluted with NaOH 2 M (8 mL) and extracted with Et2O (50 mL). Evaporation of the organic layer gave a 2:1 mixture of mono and bis-alkylated piperazine (450 mg) which was discarded. The aqueous layer was further extracted with DCM (100 mL) to give of 1-(but-3-ynyl)piperazine (640 mg).

Workup

  1. temperatureto reflux for 30 min
  2. concentrationThe mixture was concentrated
  3. additiondiluted with NaOH 2 M (8 mL)
  4. extractionextracted with Et2O (50 mL)
  5. customEvaporation of the organic layer
  6. customgave
  7. extractionThe aqueous layer was further extracted with DCM (100 mL)

Sources & evidence

ORD record
ord-8387ed94adb9408287ea3f9c30e02f6c
Source dataset
uspto-grants-2012_01
Patent number
US08093229B2

Reaction notes

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