Piperazine → 1-[3-(4-Cyanophenyl)propyl]piperazine

HRID 704406Notes

Reaction equation

HRID 704406 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11]I)=[CH:5][CH:4]=1)#[N:2].[NH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.[K]>O1CCCC1>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 4837PiperazineHCID 5462222PotassiumHCID 223906924-(3-Iodopropyl)benzonitrile

Product 1

HCID 200740911-[3-(4-Cyanophenyl)propyl]piperazineYield 66.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 250 mg of 3-(4-cyanophenyl)propyl iodide, 0.85 g of anhydrous piperazine and 0.5 g of potassium carbonated in 10 ml of tetrahydrofuran was refluxed for 2 hours. The reaction mixture was concentrated under reduced pressure and, after addition of saturated aqueous solution of sodium chloride, the residue was extracted with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 140 mg of 1-[3-(4-cyanophenyl)propyl]piperazine.

Workup

  1. temperaturewas refluxed for 2 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionafter addition of saturated aqueous solution of sodium chloride
  4. extractionthe residue was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a484f14d57764511b275d669787169ba
Source dataset
uspto-grants-1991_01
Patent number
US04987132

Reaction notes

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