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

HRID 1400328Notes

Reaction equation

HRID 1400328 reaction equation
S(=O)(=O)(O)O.Cl.[CH2:7]([C:9]1[CH:14]=[CH:13][C:12]([NH:15]N)=[CH:11][CH:10]=1)[CH3:8].[CH3:17][N:18]1[CH2:23][CH2:22][CH2:21][CH2:20][C:19]1=O>O1CCOCC1>[CH2:7]([C:9]1[CH:14]=[CH:13][C:12]2[NH:15][C:21]3[CH2:22][CH2:23][N:18]([CH3:17])[CH2:19][C:20]=3[C:11]=2[CH:10]=1)[CH3:8]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 13603N-Methyl-2-piperidoneHCID 27609704-Ethylphenylhydrazine hydrochloride

Product 1

HCID 594550988-Ethyl-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Sulfuric acid is added to a solution of 4-ethyl 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 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 provide the desired compound.

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

Sources & evidence

ORD record
ord-8fb6218b089b41feae01c766074a24f5
Source dataset
uspto-grants-2014_12
Patent number
US08906925B2

Reaction notes

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