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

HRID 2199047Notes

Reaction equation

HRID 2199047 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[NH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1>C(O)C>[C:8]([C:7]1[C:2]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[N:3][CH:4]=[CH:5][CH:6]=1)#[N:9]

Participants

4

Reactant 2

HCID 4837PiperazineHCID 810792-Chloronicotinonitrile

Product 1

HCID 27372032-(Piperazin-1-yl)pyridine-3-carbonitrileYield 42.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Chloro-3-cyanopyridine (5.5 g; 0.04 mole) was dissolved in 80 mL ethanol (warming) and piperazine (17.2 g; 0.2 mole) was combined with this solution and the whole stirred at room temperature for 18 hrs. The reaction mixture was filtered and the filtrate concentrated to a residue which was partitioned between Et2O and H2O. The water layer was made basic and extracted with Et2O. The Et2O extracts were washed with water, dried (MgSO4), concentrated to a solid which was recrystallized from Skellysolve B to yield 3.2 g product, m.p. 102°-104° C.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate concentrated to a residue which
  3. customwas partitioned between Et2O and H2O
  4. extractionextracted with Et2O
  5. washThe Et2O extracts were washed with water
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated to a solid which
  8. customwas recrystallized from Skellysolve B

Sources & evidence

ORD record
ord-9f2a1befdd654276b1e101b4cb7b946b
Source dataset
uspto-grants-1982_11
Patent number
US04361565

Reaction notes

Loading…