Potassium Carbonate → 3-Chloro-6-[4-(2,3-dimethylphenyl)-1-piperazinyl]-4,5-dimethylpyridazine

HRID 486462Notes

Reaction equation

HRID 486462 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5](Cl)=[C:6]([CH3:9])[C:7]=1[CH3:8].[CH3:11][C:12]1[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][C:13]=1[N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1.C(=O)([O-])[O-].[K+].[K+]>O.ClC(Cl)Cl>[Cl:1][C:2]1[N:3]=[N:4][C:5]([N:22]2[CH2:23][CH2:24][N:19]([C:13]3[CH:14]=[CH:15][CH:16]=[C:17]([CH3:18])[C:12]=3[CH3:11])[CH2:20][CH2:21]2)=[C:6]([CH3:9])[C:7]=1[CH3:8]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 705411-(2,3-Xylyl)piperazineHCID 211875053,6-Dichloro-4,5-dimethylpyridazine

Product 1

HCID 151246033-Chloro-6-[4-(2,3-dimethylphenyl)-1-piperazinyl]-4,5-dimethylpyridazineYield 30%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Conditions

Temperature
190 °C

Procedure

A mixture of 3.9 parts of 3,6-dichloro-4,5-dimethylpyridazine, 4.2 parts of 1-(2,3-dimethylphenyl)piperazine and 2.94 parts of potassium carbonate was stirred and heated for 4 hours in an oil bath at 190° C. After cooling, the mixture was taken up in water and trichloromethane. The organic layer was separated, dried, filtered and evaporated. The residue was crystallized from 2-propanol. The product was filtered off and dried, yielding 2 parts (30%) of 3-chloro-6-[4-(2.3-dimethylphenyl)-1-piperazinyl]-4,5-dimethylpyridazine; mp. 194.5° C. (compound 217).

Workup

  1. temperatureAfter cooling
  2. customThe organic layer was separated
  3. customdried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was crystallized from 2-propanol
  7. filtrationThe product was filtered off
  8. customdried

Sources & evidence

ORD record
ord-d3871cda59c045ba83a611d06e6986fe
Source dataset
uspto-grants-1994_03
Patent number
US05292738

Reaction notes

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