Chlorosuccinimide → HCID 22036518, compound

HRID 1789753Notes

Reaction equation

HRID 1789753 reaction equation
[Cl:1][C:2]1[C:7]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[N:6][CH:5]=[CH:4][N:3]=1.[Cl:14]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Cl:1][C:2]1[C:7]([N:8]2[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]2)=[N:6][CH:5]=[C:4]([Cl:14])[N:3]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 140864382-Chloro-3-(piperazin-1-yl)pyrazine

Product 1

HCID 22036518HCID 22036518, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a suspension of 2-chloro-3-(1-piperazinyl)pyrazine (11.7 g, 58.7 mmol; from Example 90, Step 1) in CHCl3 (50 mL) was N-chlorosuccinimid (14.4 g, 108 mmol) added and the mixture was heated at reflux for 30 minutes. The reaction mixture was cooled to ambient temperature and extracted twice with water. The combined aqueous phases were made alkaline (11M NaOH), saturated with NaCl, cooled, and extracted with EtOAc (×3). Concentration of the combined, dried (MgSO4), organic phases afforded 6.12 g (45%) of the title compound as a brown oil which crystallized upon standing: mp 89-97° C. Anal. (C8H10Cl2N4.⅓H2O)C, H, N.

Workup

  1. additionadded
  2. temperaturethe mixture was heated
  3. temperatureat reflux for 30 minutes
  4. extractionextracted twice with water
  5. temperaturesaturated with NaCl, cooled
  6. extractionextracted with EtOAc (×3)
  7. dry with materialdried (MgSO4), organic phases

Sources & evidence

ORD record
ord-1735d8f2fbc045309b6f3ada227af701
Source dataset
uspto-grants-2006_07
Patent number
US07071180B2

Reaction notes

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