1-Methylpiperidin-4-one hydrochloride → HCID 67311353, compound

HRID 1401413Notes

Reaction equation

HRID 1401413 reaction equation
Cl.[C:2]([C:6]1[CH:11]=[CH:10][C:9]([NH:12]N)=[CH:8][CH:7]=1)([CH3:5])([CH3:4])[CH3:3].Cl.[CH3:15][N:16]1[CH2:21][CH2:20][C:19](=O)[CH2:18][CH2:17]1>S(=O)(=O)(O)O.O1CCOCC1>[C:2]([C:6]1[CH:11]=[CH:10][C:9]2[NH:12][C:19]3[CH2:20][CH2:21][N:16]([CH3:15])[CH2:17][C:18]=3[C:8]=2[CH:7]=1)([CH3:5])([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 122100571-Methylpiperidin-4-one hydrochlorideHCID 162174584-Tert-butylphenylhydrazine hydrochloride

Product 1

HCID 67311353HCID 67311353, compound

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

(4-tert-Butylphenyl)hydrazine hydrochloride (1 equiv.) is taken in 7% sulfuric acid in 1,4-dioxane. 1-Methylpiperidin-4-one hydrochloride (0.76-1.4 equiv.) is added and the contents are stirred at 80° C. for 3 h. The reaction is monitored by TLC and LCMS. After completion of the reaction, the reaction mixture is concentrated and then quenched with aq. NaHCO3 solution, followed by extracted with EtOAc. The organic layer is dried over anhydrous sodium sulfate, evaporated to dryness and purified by column chromatography (5% MeOH-DCM) to afford 8-tert-butyl-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole.

Workup

  1. customAfter completion of the reaction
  2. concentrationthe reaction mixture is concentrated
  3. customquenched with aq. NaHCO3 solution
  4. extractionby extracted with EtOAc
  5. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  6. customevaporated to dryness
  7. custompurified by column chromatography (5% MeOH-DCM)

Sources & evidence

ORD record
ord-f07ccb87f3a04db18c8146a5208a99e9
Source dataset
uspto-grants-2014_12
Patent number
US08907097B2

Reaction notes

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