Acetone → 2-Chloro-5-(1-piperazinyl)pyrazine

HRID 223453Notes

Reaction equation

HRID 223453 reaction equation
Cl[C:2]1[CH:7]=[N:6][C:5]([Cl:8])=[CH:4][N:3]=1.[NH:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.CC(C)=O.Cl>O>[Cl:8][C:5]1[N:6]=[CH:7][C:2]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[N:3][CH:4]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 4837PiperazineHCID 3362242,5-Dichloropyrazine

Product 1

HCID 38220052-Chloro-5-(1-piperazinyl)pyrazineYield 36.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 2,5-dichloropyrazine (14.9 g, 0.1 mol), piperazine (50.5 g, 0.59 mol), acetone (22.5 ml), water (20 ml) and concentrated aqueous HCl (1.8 ml) was heated at reflux for 3 hr. The reaction mixture was cooled, diluted with water, filtered and the acetone was removed by distillation. The aqueous solution was then extracted thrice with chloroform. The combined extracts were washed twice with water, dried (Na2SO4) and evaporated to dryness to afford 7.3 g of solid, m.p. 98°-102°. J. K. Boissier et al., J. Med. Chem., 6, 541 (1963) report a m.p. of 101° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hr
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. customthe acetone was removed by distillation
  6. extractionThe aqueous solution was then extracted thrice with chloroform
  7. washThe combined extracts were washed twice with water
  8. dry with materialdried (Na2SO4)
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-d912770e1ccd40d1b6b8c1a24472da16
Source dataset
uspto-grants-1982_10
Patent number
US04355031

Reaction notes

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