Sodium Carbonate → HCID 15124691, compound

HRID 359427Notes

Reaction equation

HRID 359427 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5](Cl)=[CH:6][CH:7]=1.Br.Br.[F:11][C:12]([F:27])([F:26])[C:13]1[CH:14]=[C:15]([NH:19][CH:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)[CH:16]=[CH:17][CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C(=O)C>[Cl:1][C:2]1[N:3]=[N:4][C:5]([N:23]2[CH2:22][CH2:21][CH:20]([NH:19][C:15]3[CH:16]=[CH:17][CH:18]=[C:13]([C:12]([F:11])([F:26])[F:27])[CH:14]=3)[CH2:25][CH2:24]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 673313,6-DichloropyridazineHCID 19095561HCID 19095561, compound

Product 1

HCID 15124691HCID 15124691, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 3 parts of 3,6-dichloropyridazine, 6.1 parts of N-[3-(trifluoromethyl)phenyl]-4-piperidinamine dihydrobromide, 6.4 parts of sodium carbonate and 180 parts of N,N-dimethylacetamide was stirred for 24 hours at 60° C. After cooling to room temperature, the reaction mixture was poured onto water. The product was extracted with methylbenzene. The extract was washed with water, 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 pure fractions were collected and the eluent was evaporated. The residue was crystallized from 2,2'-oxybispropane. The product was filtered off and dried, yielding 2.5 parts (47%) of 1-(6-chloro-3-pyridazinyl)-N-[3-(trifluoromethyl)phenyl]-4-piperidinamine; mp. 117.9° C. (compound 148).

Workup

  1. temperatureAfter cooling to room temperature
  2. additionthe reaction mixture was poured onto water
  3. extractionThe product was extracted with methylbenzene
  4. washThe extract was washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by column chromatography over silica gel using
  9. additiona mixture of trichloromethane and methanol (97:3 by volume) as eluent
  10. customThe pure fractions were collected
  11. customthe eluent was evaporated
  12. customThe residue was crystallized from 2,2'-oxybispropane
  13. filtrationThe product was filtered off
  14. customdried

Sources & evidence

ORD record
ord-bce4be0ac8874890b82de4ddfb15c221
Source dataset
uspto-grants-1991_03
Patent number
US05001125

Reaction notes

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