Sulfuric Acid → HCID 59455170, compound

HRID 1401415Notes

Reaction equation

HRID 1401415 reaction equation
S(=O)(=O)(O)O.Cl.[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14]N)=[CH:10][CH:9]=1.[CH:16]1([N:19]2[CH2:24][CH2:23][CH2:22][CH2:21][C:20]2=O)[CH2:18][CH2:17]1>O1CCOCC1>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]2[NH:14][C:22]3[CH2:23][CH2:24][N:19]([CH:16]4[CH2:18][CH2:17]4)[CH2:20][C:21]=3[C:10]=2[CH:9]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 71600Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1)HCID 22021808HCID 22021808, compound

Product 1

HCID 59455170HCID 59455170, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Sulfuric acid is added to a solution of 4-Chloro phenyl hydrazine hydrochloride (1 equiv.) in dioxane and stirred for 5 min. at RT. N-cyclopropyl piperidone (1 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 product 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 product is extracted with EtOAc
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customevaporator

Sources & evidence

ORD record
ord-3f862be33d5344a081f1d7fde7bca34f
Source dataset
uspto-grants-2014_12
Patent number
US08907097B2

Reaction notes

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