Sodium Carbonate → HCID 15124730, compound

HRID 486454Notes

Reaction equation

HRID 486454 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5](Cl)=[CH:6][CH:7]=1.[F:9][C:10]([F:25])([F:24])[C:11]1[CH:12]=[C:13]([NH:17][CH:18]2[CH2:23][CH2:22][CH2:21][NH:20][CH2:19]2)[CH:14]=[CH:15][CH:16]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[Cl:1][C:2]1[N:3]=[N:4][C:5]([N:20]2[CH2:21][CH2:22][CH2:23][CH:18]([NH:17][C:13]3[CH:14]=[CH:15][CH:16]=[C:11]([C:10]([F:9])([F:25])[F:24])[CH:12]=3)[CH2:19]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 673313,6-DichloropyridazineHCID 19095529HCID 19095529, compound

Product 1

HCID 15124730HCID 15124730, compoundYield 16.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 4.5 parts of 3,6-dichloropyridazine, 4.9 parts of N-[3-(trifluoromethyl)phenyl]-3-piperidinamine, 6.4 parts of sodium carbonate and 180 parts of N,N-dimethylformamide was stirred overnight at about 65° C. The reaction mixture was poured into ice water and the product was extracted with dichloromethane. The extract was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (99:1 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from 2-propanol. The product was filtered off (the filtrate was set aside) and dried, yielding 1.2 parts (16.8%) of 1-(6-chloro-3-pyridazinyl)-N-[3-(trifluoromethyl}phenyl]-3-piperidinamine: mp. 92.6° C. (compound 146). The filtrate, which was set aside, was converted into the hydrochloride salt in 2-propanol. The salt was filtered off and dried, yielding 2.6 parts (32.9%) of 1-(6-chloro-3-pyridazinyl)-N-[3-(trifluoromethyl)-phenyl]-3-piperidinamine monohydrochloride; mp. 173.5° C. (compound 147).

Workup

  1. extractionthe product was extracted with dichloromethane
  2. customThe extract was dried
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by column chromatography over silica gel using
  6. additiona mixture of trichloromethane and methanol (99:1 by volume) as eluent
  7. customThe pure fractions were collected
  8. customthe eluent was evaporated
  9. customThe residue was crystallized from 2-propanol
  10. filtrationThe product was filtered off (the filtrate
  11. customdried

Sources & evidence

ORD record
ord-f10c9e5875f84f2ea277ce367589de71
Source dataset
uspto-grants-1994_03
Patent number
US05292738

Reaction notes

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