1-(4-Pyridyl)piperazine → HCID 54076201, compound

HRID 1066566Notes

Reaction equation

HRID 1066566 reaction equation
[CH3:1][O:2][C:3](=[O:18])[CH:4]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1)[CH2:5][C:6]([OH:8])=O.O.ON1C2C=CC=CC=2N=N1.[N:30]1[CH:35]=[CH:34][C:33]([N:36]2[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]2)=[CH:32][CH:31]=1>C(#N)C>[CH3:1][O:2][C:3](=[O:18])[CH:4]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1)[CH2:5][C:6](=[O:8])[N:39]1[CH2:40][CH2:41][N:36]([C:33]2[CH:34]=[CH:35][N:30]=[CH:31][CH:32]=2)[CH2:37][CH2:38]1

Participants

5

Reactant 3

HCID 705171-(4-Pyridyl)piperazineHCID 27960291-Hydroxybenzotriazole hydrateHCID 45490076HCID 45490076, compound

Product 1

HCID 54076201HCID 54076201, compoundYield 89.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-(4-methoxybenzyl)succinic acid 1-methyl ester (3 g) in acetonitrile (60 ml) were added HOBt (1-hydroxy-1H-benzotriazole monohydrate) (1.84 g) and 1-ethyl-3-(3-dimethylamgnopropyl)carbodiide hydrochloride (2.76 g) and the solution was stirred for 10 minutes. To the solution was added 1-(4-pyridyl)-piperazine (1.96 g) and the solution was stirred for 30 minutes at room temperature. The reaction mixture was concentrated and the concentrate was made basic with an aqueous solution of sodium hydrogen carbonate to give an alkaline solution, which was extracted with ethyl acetate twice. The extract was washed with saturated brine and dried over Na2SO4. The solution was concentrated under reduced pressure and recrystallized from ethyl acetate/hexane to give the titled compound (4.25 g) as colorless needles.

Workup

  1. stirringthe solution was stirred for 30 minutes at room temperature
  2. concentrationThe reaction mixture was concentrated
  3. customto give an alkaline solution, which
  4. extractionwas extracted with ethyl acetate twice
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over Na2SO4
  7. concentrationThe solution was concentrated under reduced pressure
  8. customrecrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-655bea7c45f14a3192c2baebea7ba09b
Source dataset
uspto-grants-2001_06
Patent number
US06242600B1

Reaction notes

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