Chloroform → HCID 19814216, compound

HRID 466567Notes

Reaction equation

HRID 466567 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([NH:8]C(=O)C)=[CH:4][CH:3]=1.[CH3:12][C:13]1[CH:14]=[C:15]([N:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[CH:16]=[CH:17][CH:18]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:31]C(Cl)Cl>O>[ClH:1].[ClH:31].[CH3:12][C:13]1[CH:14]=[C:15]([N:19]2[CH2:24][CH2:23][N:22]([C:2]3[N:7]=[N:6][C:5]([NH2:8])=[CH:4][CH:3]=3)[CH2:21][CH2:20]2)[CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 11430Potassium CarbonateHCID 831111-(m-Tolyl)piperazineHCID 19095604N-(6-Chloropyridazin-3-yl)acetamide

Product 1

HCID 19814216HCID 19814216, compoundYield 6.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 3.5 parts of N-(6-chloro-3-pyridazinyl)acetamide, 3.6 parts of 1-(3-methylphenyl)piperazine and 2.8 parts of potassium carbonate was stirred for 7 hours in an oil bath at 160° C. After cooling, trichloromethane and water were added. The layers were separated. The organic layer was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (97:3 by volume) as eluent. The second fraction was collected and the eluent was evaporated. The residue was converted into the hydrochloride salt in 2-propanol and 2-propanone. The salt was filtered off and dried, yielding 0.5 parts (6.6%) of 6-[4-(3-methylphenyl)-1-piperazinyl]-3-pyridazinamine dihydrochloride; mp. 178.5° C. (compound 220).

Workup

  1. temperatureAfter cooling
  2. customThe layers were separated
  3. customThe organic layer was dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column chromatography over silica gel using
  7. additiona mixture of trichloromethane and methanol (97:3 by volume) as eluent
  8. customThe second fraction was collected
  9. customthe eluent was evaporated
  10. filtrationThe salt was filtered off
  11. customdried

Sources & evidence

ORD record
ord-e82bdf66362d4d1c8741897370f57d8f
Source dataset
uspto-grants-1992_10
Patent number
US05157035

Reaction notes

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