1-Phenylpiperazine → 1-(But-3-yn-1-yl)-4-phenylpiperazine

HRID 375534Notes

Reaction equation

HRID 375534 reaction equation
C(OS([C:9]1[CH:14]=[CH:13][C:12](C)=[CH:11][CH:10]=1)(=O)=O)CC#C.[C:16]1([N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)C=C[CH:19]=[CH:18][CH:17]=1.C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH2:16]([N:22]1[CH2:27][CH2:26][N:25]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:24][CH2:23]1)[CH2:17][C:18]#[CH:19]

Participants

5

Reactant 3

HCID 70961-PhenylpiperazineHCID 2720203-Butynyl p-toluenesulfonateHCID 516892Sodium Bicarbonate

Product 1

HCID 189930381-(But-3-yn-1-yl)-4-phenylpiperazineYield 78.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of but-3-ynyl-p-toluenesulfonate (8.97 g), 1-phenylpiperazine (6.49 g) and sodium bicarbonate (3.7 g) in dimethylformamide (100 mL) is stirred at 80° C. for 14 hours. The solvent is evaporated and the residue dissolved in dichloromethane, washed with water and dried over MgSO4. The solution is filtered through silica gel and the product eluted with 10% ethyl acetate/hexanes to give 6.76 g of the title compound as a white solid.

Workup

  1. customThe solvent is evaporated
  2. dissolutionthe residue dissolved in dichloromethane
  3. washwashed with water
  4. dry with materialdried over MgSO4
  5. filtrationThe solution is filtered through silica gel
  6. washthe product eluted with 10% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-1b1257d60573427cb265f52a07432601
Source dataset
uspto-grants-1996_01
Patent number
US05486517

Reaction notes

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