Hydrochloric Acid → HCID 178424551, compound

HRID 486475Notes

Reaction equation

HRID 486475 reaction equation
O[C:2]1([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[CH:16]=2)[CH2:7][CH2:6][N:5]([C:8]2[N:13]=[N:12][C:11]([OH:14])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.Cl>C(O)C>[CH3:21][C:17]1[CH:16]=[C:15]([C:2]2[CH2:7][CH2:6][N:5]([C:8]3[N:13]=[N:12][C:11]([OH:14])=[CH:10][CH:9]=3)[CH2:4][CH:3]=2)[CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178424721HCID 178424721, compound

Product 1

HCID 178424551HCID 178424551, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2.9 parts of 6-[4-hydroxy-4-(3-methylphenyl)-1-piperidinyl]-3-pyridazinol, 30 parts of a hydrochloric acid solution 6N and 24 parts of ethanol was stirred for 2 hours at reflux temperature. The reaction mixture was evaporated. Crushed ice was added and the whole was treated with concentrate ammonium hydroxide. The product was extracted with trichloromethane. The extract was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (98:2 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from a mixture of 2-propanol and 2.2'-oxybispropane. The product was filtered off and dried, yielding 2 parts (75%) of 6-[3,6-dihydro-4-(3-methylphenyl)-1(2H)-pyridinyl]-3-pyridazinol; mp. 179.0° C. (compound 270).

Workup

  1. temperatureat reflux temperature
  2. customThe reaction mixture was evaporated
  3. additionCrushed ice was added
  4. additionthe whole was treated with concentrate ammonium hydroxide
  5. extractionThe product was extracted with trichloromethane
  6. customThe extract was dried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by column chromatography over silica gel using
  10. additiona mixture of trichloromethane and methanol (98:2 by volume) as eluent
  11. customThe pure fractions were collected
  12. customthe eluent was evaporated
  13. customThe residue was crystallized from a mixture of 2-propanol and 2.2'-oxybispropane
  14. filtrationThe product was filtered off
  15. customdried

Sources & evidence

ORD record
ord-e7f3f02c57624ee7a1a6fd07f26f80d8
Source dataset
uspto-grants-1994_03
Patent number
US05292738

Reaction notes

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