Piperazine → 1-(3-Piperazinylpropyl)-3-n-hexylurea

HRID 543186Notes

Reaction equation

HRID 543186 reaction equation
Cl[CH2:2][CH2:3][CH2:4][NH:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[O:7].[NH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1>C(O)C>[N:15]1([CH2:2][CH2:3][CH2:4][NH:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[O:7])[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 136067321-(3-Chloropropyl)-3-n-hexylurea

Product 1

HCID 571432471-(3-Piperazinylpropyl)-3-n-hexylureaYield 39%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-(3-chloropropyl)-3-n-hexylurea (11.0 g; 50 mmole), piperazine (43.0 g; 500 mmole) and reagent ethanol (250 ml) was refluxed for 2 hours. The solvent was removed in vacuo, and the solid residue was dissolved in water. The resulting solution was extracted with methylene chloride, concentrated in vacuo, and the residue was chromatographed on silica gel to give 1-(3-piperazinylpropyl)-3-n-hexylurea as a light yellow oil (6.7 g; 39% yield).

Workup

  1. temperaturewas refluxed for 2 hours
  2. customThe solvent was removed in vacuo
  3. dissolutionthe solid residue was dissolved in water
  4. extractionThe resulting solution was extracted with methylene chloride
  5. concentrationconcentrated in vacuo
  6. customthe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-f3e9bad033cb48e59cad608a7162c03c
Source dataset
uspto-grants-1987_04
Patent number
US04661481

Reaction notes

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