Hydrochloric Acid → HCID 59442809, compound

HRID 243569Notes

Reaction equation

HRID 243569 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([C:10]2[N:15]=[N:14][C:13]([N:16]3[CH2:25][CH2:24][C:19]4(OCC[O:20]4)[CH2:18][CH2:17]3)=[CH:12][CH:11]=2)[CH:6]=[CH:7][C:8]=1[Cl:9]>O.[OH-].[Na+]>[Cl:2][C:3]1[CH:4]=[C:5]([C:10]2[N:15]=[N:14][C:13]([N:16]3[CH2:17][CH2:18][C:19](=[O:20])[CH2:24][CH2:25]3)=[CH:12][CH:11]=2)[CH:6]=[CH:7][C:8]=1[Cl:9]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59442792HCID 59442792, compound

Product 1

HCID 59442809HCID 59442809, compoundYield 84.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
60 °C

Procedure

M HCl (10 ml) is added to a mixture of 8-(6-(3,4-dichlorophenyl)pyridazin-3-yl)-1,4-dioxa-8-azaspiro[4.5]decane (500 mg) in water (5 ml). The mixture is stirred for 1 hour at 60° C., cooled to room temperature, diluted with water and neutralized with 4 N NaOH. The aqueous layer is extracted with EtOAc (3×). The combined organic layers are washed with brine, dried (Na2SO4) and filtered, and the solvent is removed under reduced pressure to give 1-(6-(3,4-dichlorophenyl)pyridazin-3-yl)piperidin-4-one (370 mg). m/z(+) 322/324/326 (M+H+).

Workup

  1. temperaturecooled to room temperature
  2. extractionThe aqueous layer is extracted with EtOAc (3×)
  3. washThe combined organic layers are washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-545d832885224611880d7fc5ec2645d5
Source dataset
uspto-grants-2014_02
Patent number
US08653262B2

Reaction notes

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