Hydrazine → 4-(2-Pyrimidinyl)-1-piperazinebutanamine

HRID 905171Notes

Reaction equation

HRID 905171 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[N:7]1[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][CH2:15][C:16]#[N:17])[CH2:9][CH2:8]1.NN>C(O)(C)C.[Ni].C(O)C>[NH2:17][CH2:16][CH2:15][CH2:14][CH2:13][N:10]1[CH2:9][CH2:8][N:7]([C:2]2[N:1]=[CH:6][CH:5]=[CH:4][N:3]=2)[CH2:12][CH2:11]1

Participants

6

Reactant 2

HCID 9321HydrazineHCID 3986541-Piperazinebutanenitrile, 4-(2-pyrimidinyl)-

Product 1

HCID 128407054-(2-Pyrimidinyl)-1-piperazinebutanamineYield 68.1%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 3776IsopropanolSolvent

Procedure

4-[4-(2-Pyrimidinyl)-1-piperazinyl]butyronitrile (115.7 g; 0.5 mole) was dissolved in 1.5 L isopropyl alcohol. Approximately 50 mL of a suspension of Raney nickel in anhydrous ethanol was added and the resulting reaction mixture was heated to reflux and hydrazine (120 g) was slowly added dropwise. On completion of the reaction, the spent catalyst was removed by filtration and the filtrate was concentrated in vacuo to a yellow oil which was distilled to yield 80.1 g (60%) of product, boiling point 135°-145° C. at 0.10 mm. (The nitrile used in this reaction is described in Wu, et al., Journal of Medicinal Chemistry, 15, page 477-479 (1972).)

Workup

  1. customthe resulting reaction mixture
  2. temperaturewas heated
  3. temperatureto reflux
  4. customOn completion of the reaction
  5. customthe spent catalyst was removed by filtration
  6. concentrationthe filtrate was concentrated in vacuo to a yellow oil which
  7. distillationwas distilled

Sources & evidence

ORD record
ord-91b3ccf281254951b66486c1e8688223
Source dataset
uspto-grants-1983_12
Patent number
US04423049

Reaction notes

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