Sodium Iodide → HCID 14989359, compound

HRID 1030938Notes

Reaction equation

HRID 1030938 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16]Cl)[CH2:10][CH2:9]2)=[CH:6][CH:7]=1.[I-].[Na+].[Cl:20][C:21]1[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=[CH:23][C:22]=1[OH:29].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:1][C:2]1[N:3]=[N:4][C:5]([N:8]2[CH2:9][CH2:10][CH:11]([CH2:14][CH2:15][CH2:16][O:29][C:22]3[CH:23]=[CH:24][C:25]([O:27][CH3:28])=[CH:26][C:21]=3[Cl:20])[CH2:12][CH2:13]2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 874592-Chloro-4-methoxyphenolHCID 14989321HCID 14989321, compound

Product 1

HCID 14989359HCID 14989359, compoundYield 41.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 3.0 parts of 3-chloro-6-[4-(3-chloropropyl)-1-piperidinyl]pyridazine in 80 parts of acetonitrile were added 2.1 parts of sodium iodide. The reaction mixture was stirred for 2 hours at reflux temperature. After cooling, a mixture of 2.2 parts of 2-chloro-4-methoxyphenol and 3.8 parts of potassium carbonate was added to the mixture and the whole was stirred for 2 days at reflux temperature. The reaction mixture was evaporated and the residue was taken up in water. 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 and dried at 70° C., yielding 1.8 parts (41.3%) of 3-chloro-6-[4-[3-(2-chloro-4-methoxyphenoxy)propyl]-1-piperidinyl]pyridazine; mp. 101.0° C. (comp. 141).

Workup

  1. temperatureat reflux temperature
  2. temperatureAfter cooling
  3. additionwas added to the mixture
  4. stirringthe whole was stirred for 2 days
  5. temperatureat reflux temperature
  6. customThe reaction mixture was evaporated
  7. extractionThe product was extracted with dichloromethane
  8. customThe extract was dried
  9. filtrationfiltered
  10. customevaporated
  11. customThe residue was purified by column chromatography over silica gel using
  12. additiona mixture of trichloromethane and methanol (99:1 by volume) as eluent
  13. customThe pure fractions were collected
  14. customthe eluent was evaporated
  15. customThe residue was crystallized from 2-propanol
  16. filtrationThe product was filtered off
  17. customdried at 70° C.

Sources & evidence

ORD record
ord-1a45119eea7442728c66d360b3bdc2df
Source dataset
uspto-grants-1992_04
Patent number
US05106973

Reaction notes

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