Piperazine → 2-(Piperazin-1-yl)pyridine-3-carbonitrile

HRID 1381108Notes

Reaction equation

HRID 1381108 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl[C:8]1[C:13]([C:14]#[N:15])=[CH:12][CH:11]=[CH:10][N:9]=1>C(O)C>[C:14]([C:13]1[C:8]([N:1]2[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]2)=[N:9][CH:10]=[CH:11][CH:12]=1)#[N:15]

Participants

4

Reactant 2

HCID 4837PiperazineHCID 810792-Chloronicotinonitrile

Product 1

HCID 27372032-(Piperazin-1-yl)pyridine-3-carbonitrileYield 72.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of piperazine (0.5 mol) and 2-chloro-3-cyanopyridine (0.1 mol) in absolute ethanol (225 ml) was heated at reflux for 16 hours. The cooled mixture was filtered to remove precipitated piperazine hydrochloride and the filtrate evaporated in vacuo. The residue was diluted with water (200 ml), made basic (pH>10) with 5N sodium hydroxide and extracted with ether (5×300 ml). The combined extracts were dried (MgSO4) and evaporated in vacuo affording 13.6 g of a white solid (72.5% yield); mp 99°-103° C. Spectral data are consistent with the assigned structure. This material was used without further purification.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 hours
  3. filtrationThe cooled mixture was filtered
  4. customto remove
  5. customprecipitated piperazine hydrochloride
  6. customthe filtrate evaporated in vacuo
  7. additionThe residue was diluted with water (200 ml)
  8. extractionextracted with ether (5×300 ml)
  9. dry with materialThe combined extracts were dried (MgSO4)
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-d62e1a7ac55549b5b5f2d3d825b1ec91
Source dataset
uspto-grants-1986_04
Patent number
US04585773

Reaction notes

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