1-Methyl-4-piperidone → HCID 59455254, compound

HRID 1400326Notes

Reaction equation

HRID 1400326 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[C:7]([Cl:9])[CH:6]=[CH:5][C:4]=1[NH:10]N.[CH3:12][N:13]1[CH2:18][CH2:17][C:16](=O)[CH2:15][CH2:14]1>OS(O)(=O)=O.O1CCOCC1>[Cl:2][C:3]1[C:4]2[NH:10][C:16]3[CH2:17][CH2:18][N:13]([CH3:12])[CH2:14][C:15]=3[C:5]=2[CH:6]=[C:7]([Cl:9])[CH:8]=1

Participants

5

Reactant 2

HCID 740491-Methyl-4-piperidoneHCID 2723905(2,4-Dichlorophenyl)hydrazine monohydrochloride

Product 1

HCID 59455254HCID 59455254, compoundYield 48.6%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

2,4-Dichlorophenylhydrazine hydrochloride (1.0 g, 4.68 mmol) was dissolved in 7% H2SO4 in 1,4-dioxan (50 mL) and N-methylpiperidine-4-one (0.76 g, 5.0 mmol) was added and stirred at RT for 15 min, heated at 80° C. for 14 h. After completion of the reaction (monitored by LCMS), solvent was removed in vacuum, basified with saturated aq. NaHCO3 and extracted with EtOAc. Organic layer was separated, dried over anhydrous sodium sulfate and concentrated under vacuum. The resulting product was purified by column chromatography to afford 0.58 g of 6,8-dichloro-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole.

Workup

  1. temperatureheated at 80° C. for 14 h
  2. customAfter completion of the reaction (monitored by LCMS), solvent
  3. customwas removed in vacuum
  4. extractionextracted with EtOAc
  5. customOrganic layer was separated
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under vacuum
  8. customThe resulting product was purified by column chromatography

Sources & evidence

ORD record
ord-11351f83703d43ac909ea6ce5732e92c
Source dataset
uspto-grants-2014_12
Patent number
US08906925B2

Reaction notes

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