Piperazine → 1-(2-Propynyl)piperazine

HRID 1990910Notes

Reaction equation

HRID 1990910 reaction equation
[CH2:1](Br)[C:2]#[CH:3].[NH:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1>C1COCC1.O>[CH2:1]([N:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1)[C:2]#[CH:3]

Participants

5

Reactant 2

HCID 4837PiperazineHCID 7842Propargyl bromide

Product 1

HCID 146273691-(2-Propynyl)piperazineYield 23%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Propargyl bromide (1.19 g, 10 mmol) and piperazine (8.61 g, 100 mmol) were dissolved in THF (90 ml). Stir under N2 and reflux for 4 h. Remove solvent and dissolve in 40 ml of H2O. Extracted with 4×40 ml of EtOAc, washed with 2×15 ml of brine, dried over MgSO4. After solvent was removed, brownish solid 29.83 (285 mg, 23% yield) was obtained. 1H NMR (CDCl3, 200 MHz): δ=2.28 (t, 1H, J=2.4 Hz), 2.56 (m, 4H), 2.92 (m, 4H), 3.30 (d, 2H, J=2.6 Hz).

Workup

  1. temperaturereflux for 4 h
  2. extractionExtracted with 4×40 ml of EtOAc
  3. washwashed with 2×15 ml of brine
  4. dry with materialdried over MgSO4
  5. customAfter solvent was removed

Sources & evidence

ORD record
ord-3273fde7245245c4be00b5144e1f8574
Source dataset
uspto-grants-2010_01
Patent number
US07645754B2

Reaction notes

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