Piperazine → 1-(3-Phenylprop-2-yn-1-yl)piperazine

HRID 1990911Notes

Reaction equation

HRID 1990911 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Br[CH2:8][C:9]#[C:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C1COCC1>[C:11]1([C:10]#[C:9][CH2:8][N:1]2[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 10987157(3-Bromoprop-1-yn-1-yl)benzene

Product 1

HCID 607995831-(3-Phenylprop-2-yn-1-yl)piperazineYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of piperazine (862 mg, 10.0 mmol) in THF (16 mL) is added (3-bromoprop-1-ynyl)-benzene (245 mg, 1.26 mmol), and the reaction mixture is stirred overnight. THF is evaporated, water/Na2CO3 is added, the mixture is extracted with Et2O (6×10 mL), the combined extracts are washed with water, brine, dried over MgSO4, filtered, and concentrated. The residue is purified by chromatography (silica gel, MeOH/CH2Cl2), yielding 179 mg (0.892 mmol, 71%) of the target compound. 1H NMR (CDCl3, 200 MHz): δ=1.97 (s, 1H), 2.63 (m, 4H), 2.97 (m, 4H), 3.51 (s, 2H), 7.25-7.35 (m, 3H), 7.40-7.48 (m, 2H).

Workup

  1. customTHF is evaporated
  2. additionwater/Na2CO3 is added
  3. extractionthe mixture is extracted with Et2O (6×10 mL)
  4. washthe combined extracts are washed with water, brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue is purified by chromatography (silica gel, MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-2a4add1650d7421b9a2b9d69e46f9e6c
Source dataset
uspto-grants-2010_01
Patent number
US07645754B2

Reaction notes

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