Sulfuric Acid → HCID 919384, compound

HRID 1401416Notes

Reaction equation

HRID 1401416 reaction equation
S(=O)(=O)(O)O.Cl.[F:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14]N)=[CH:10][CH:9]=1.[CH3:16][N:17]1[CH2:22][CH2:21][CH2:20][CH2:19][C:18]1=O>O1CCOCC1>[F:7][C:8]1[CH:13]=[CH:12][C:11]2[NH:14][C:20]3[CH2:21][CH2:22][N:17]([CH3:16])[CH2:18][C:19]=3[C:10]=2[CH:9]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 13603N-Methyl-2-piperidoneHCID 699814-Fluorophenylhydrazine hydrochloride

Product 1

HCID 919384HCID 919384, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Sulfuric acid is added to a solution of 4-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 2 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. The reaction mixture is extracted with EtOAc, dried over anhydrous sodium sulfate and concentrated under reduced pressure using rotary evaporator to provide the desired compound.

Workup

  1. temperaturethe mixture is heated at 80° C. for 2 h
  2. concentrationthe reaction mixture is concentrated under reduced pressure and basified to pH 10
  3. extractionThe reaction mixture is extracted with EtOAc
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customevaporator

Sources & evidence

ORD record
ord-bcc67513713f4d82940148ec987a0100
Source dataset
uspto-grants-2014_12
Patent number
US08907097B2

Reaction notes

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