Sulfuric Acid → 2,3,4,5-tetrahydro-8-isopropyl-2-methyl-1H-pyrido[4,3-b]indole

HRID 1400329Notes

Reaction equation

HRID 1400329 reaction equation
S(=O)(=O)(O)O.Cl.[CH:7]([C:10]1[CH:15]=[CH:14][C:13]([NH:16]N)=[CH:12][CH:11]=1)([CH3:9])[CH3:8].[CH3:18][N:19]1[CH2:24][CH2:23][CH2:22][CH2:21][C:20]1=O>O1CCOCC1>[CH:7]([C:10]1[CH:15]=[CH:14][C:13]2[NH:16][C:22]3[CH2:23][CH2:24][N:19]([CH3:18])[CH2:20][C:21]=3[C:12]=2[CH:11]=1)([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 13603N-Methyl-2-piperidoneHCID 2733248[4-(Propan-2-yl)phenyl]hydrazine hydrochloride

Product 1

HCID 594552192,3,4,5-tetrahydro-8-isopropyl-2-methyl-1H-pyrido[4,3-b]indole

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Sulfuric acid is added to a solution of 4-isopropyl phenyl 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, 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. extractionextracted with EtOAc
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customevaporator

Sources & evidence

ORD record
ord-3c9d38ebcfba44cab42dbab1a7a9b276
Source dataset
uspto-grants-2014_12
Patent number
US08906925B2

Reaction notes

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