Piperazine → 3-Chloro-6-(1-piperazinyl)pyridazine

HRID 389042Notes

Reaction equation

HRID 389042 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[Cl:7][C:8]1[N:9]=[N:10][C:11](Cl)=[CH:12][CH:13]=1>CC(=O)CC>[Cl:7][C:8]1[N:9]=[N:10][C:11]([N:1]2[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]2)=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 673313,6-Dichloropyridazine

Product 1

HCID 52949263-Chloro-6-(1-piperazinyl)pyridazineYield 81%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
62 °C

Procedure

Piperazine (20.0 g, 232 mmol) and 3,6-dichloropyridazine (34.6 g, 232 mmol) were mixed with 2-butanone and heated at 62° C. for 16 h. The reaction mixture was cooled to room temperature and the precipitated product filtered and washed with 2-butanone. The solid was redissolved in DCM (250 mL), filtered and the filtrate evaporated. The solid was dried in vacuo to yield 37.3 g, 81% 3-chloro-6-piperazin-1-ylpyridazine.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationthe precipitated product filtered
  3. washwashed with 2-butanone
  4. dissolutionThe solid was redissolved in DCM (250 mL)
  5. filtrationfiltered
  6. customthe filtrate evaporated
  7. customThe solid was dried in vacuo

Sources & evidence

ORD record
ord-7d4aea1a6aa04db58dae608589bddbed
Source dataset
uspto-grants-2013_02
Patent number
US08378097B2

Reaction notes

Loading…