Water → HCID 14989381, compound

HRID 1030942Notes

Reaction equation

HRID 1030942 reaction equation
[OH-].[K+].O.[Cl:4][C:5]1[N:10]=[N:9][C:8]([N:11]2[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][CH2:19][O:20][C:21]3[CH:31]=[CH:30][C:24]([C:25]([O:27]CC)=[O:26])=[CH:23][CH:22]=3)[CH2:13][CH2:12]2)=[CH:7][CH:6]=1>C(O)C>[Cl:4][C:5]1[N:10]=[N:9][C:8]([N:11]2[CH2:12][CH2:13][CH:14]([CH2:17][CH2:18][CH2:19][O:20][C:21]3[CH:22]=[CH:23][C:24]([C:25]([OH:27])=[O:26])=[CH:30][CH:31]=3)[CH2:15][CH2:16]2)=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 14989252Ethyl 4-[3-[1-(6-chloro-3-pyridazinyl)-4-piperidinyl]propoxy]benzoate

Product 1

HCID 14989381HCID 14989381, compoundYield 18.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 4.5 parts of potassium hydroxide in 50 parts of water was added dropwise a solution of 4 parts of ethyl 4-[3-[1-(6-chloro-3-pyridazinyl)-4-piperidinyl]propoxy]benzoate in 160 parts of ethanol. Upon complete addition, stirring was continued over weekend at room temperature. The precipitated product was filtered off, washed with water and then stirred in water. The whole was neutralized with acetic acid. The product was filtered off, washed with water and converted into the hydrochloride salt in methanol. The crystallized product was filtered off and the filtrate was evaporated. The residue and the crystallized product were combined and stirred into water and sodium hydroxide. The precipitate was filtered off and the filtrate was treated with acetic acid. The precipitated product was filtered off, washed with water and crystallized from N,N-dimethylformamide. The product was filtered off and dried, yielding 0.7 parts (18.6%) of 4-[3-[1-(6-chloro-3-pyridazinyl)-4-piperidinyl]propoxy]benzoic acid; mp. 209.4° C. (comp. 166).

Workup

  1. additionUpon complete addition
  2. waitwas continued over weekend at room temperature
  3. filtrationThe precipitated product was filtered off
  4. washwashed with water
  5. stirringstirred in water
  6. filtrationThe product was filtered off
  7. washwashed with water
  8. filtrationThe crystallized product was filtered off
  9. customthe filtrate was evaporated
  10. stirringstirred into water and sodium hydroxide
  11. filtrationThe precipitate was filtered off
  12. additionthe filtrate was treated with acetic acid
  13. filtrationThe precipitated product was filtered off
  14. washwashed with water
  15. customcrystallized from N,N-dimethylformamide
  16. filtrationThe product was filtered off
  17. customdried

Sources & evidence

ORD record
ord-28ca773bb2da455199d56a0e705e5869
Source dataset
uspto-grants-1992_04
Patent number
US05106973

Reaction notes

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