Sulfuric Acid → HCID 59455218, compound

HRID 1401407Notes

Reaction equation

HRID 1401407 reaction equation
S(=O)(=O)(O)O.Cl.[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14]N)=[CH:10][C:9]=1[F:16].[CH3:17][N:18]1[CH2:23][CH2:22][CH2:21][CH2:20][C:19]1=O>O1CCOCC1>[Cl:7][C:8]1[C:9]([F:16])=[CH:10][C:11]2[NH:14][C:21]3[CH2:22][CH2:23][N:18]([CH3:17])[CH2:19][C:20]=3[C:12]=2[CH:13]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 13603N-Methyl-2-piperidoneHCID 53413990(4-Chloro-3-fluorophenyl)hydrazine--hydrogen chloride (1/1)

Product 1

HCID 59455218HCID 59455218, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Sulfuric acid is added to a solution of 4-chloro-3-fluorophenyl hydrazine hydrochloride (1 equiv.) in dioxane, and stirred for 5 min. at RT. N-Methyl piperidone (0.76-1.4 equiv.) is added and the mixture is heated at 80° C. for 3 h. After completion, as monitored by TLC, the reaction mixture is concentrated under reduced pressure and basified to pH 10 using 10% aqueous KOH solution, extracted with EtOAc, dried over anhydrous sodium sulfate and concentrated under reduced pressure using rotary evaporator to give a mixture or regioisomeric products. For this Example, silica gel chromatography separates the title compound from the other regioisomer (Compound 4) obtained in Example 10.

Workup

  1. temperaturethe mixture is heated at 80° C. for 3 h
  2. concentrationthe reaction mixture is concentrated under reduced pressure and basified to pH 10
  3. extractionextracted with EtOAc
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customevaporator
  7. customto give a mixture or regioisomeric products

Sources & evidence

ORD record
ord-04ffd5bd47b5497f92e92fbc6a7eafd7
Source dataset
uspto-grants-2014_12
Patent number
US08907097B2

Reaction notes

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