Sodium Acetate → HCID 14989225, compound

HRID 981639Notes

Reaction equation

HRID 981639 reaction equation
Cl[C:2]1[N:7]=[N:6][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16][OH:17])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C([O-])(=[O:20])C.[Na+]>C(O)(=O)C>[OH:17][CH2:16][CH2:15][CH2:14][CH:11]1[CH2:12][CH2:13][N:8]([C:5]2[CH:4]=[CH:3][C:2](=[O:20])[NH:7][N:6]=2)[CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 14989224HCID 14989224, compound

Product 1

HCID 14989225HCID 14989225, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 6 parts of 1-(6-chloro-3-pyridazinyl)-4-piperidinepropanol, 1.9 parts of sodium acetate and 150 parts of acetic acid was stirred for 4 hours at reflux temperature. The reaction mixture was evaporated and the residue was taken up in 200 parts of a hydrochloric acid solution 10%. After stirring for 1 hour at reflux temperature, the whole was evaporated. The residue was taken up in water and treated with ammonium hydroxide. The product was extracted with dichloromethane. The extract was dried, filtered and evaporated, yielding a first fraction of 6-[4-(3-hydroxypropyl)-1-piperidinyl]-3(2H)-pyridazinone; From the remaining aqueous layer, the precipitated product was filtered off and crystallized from 2-propanol. The product was filtered off and dried at 60° C., yielding a second fraction of the desired intermediate.

Workup

  1. temperatureat reflux temperature
  2. customThe reaction mixture was evaporated
  3. stirringAfter stirring for 1 hour
  4. temperatureat reflux temperature
  5. customthe whole was evaporated
  6. additiontreated with ammonium hydroxide
  7. extractionThe product was extracted with dichloromethane
  8. customThe extract was dried
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-15f9105fed3f4bebb63ca5bff91ee453
Source dataset
uspto-grants-1991_02
Patent number
US04992433

Reaction notes

Loading…