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

HRID 1401401Notes

Reaction equation

HRID 1401401 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>S(=O)(=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, compound

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

2,4-Dichlorophenyl hydrazine hydrochloride (1 equiv.) is taken in 7% sulfuric acid in 1,4-dioxan. N-Methylpiperidine-4-one (0.76-1.4 equiv.) is added and the contents are stirred at RT for 15 min., followed by heating at 80° C. for 14 h. After completion of the reaction, as monitored by LCMS, the solvent is removed in vacuo, basified with saturated aq. NaHCO3 and extracted with EtOAc. The organic layer is separated, dried over anhydrous sodium sulfate and concentrated. The resulting crude product is purified by column chromatography to afford 6,8-dichloro-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole.

Workup

  1. temperatureby heating at 80° C. for 14 h
  2. customAfter completion of the reaction
  3. customthe solvent is removed in vacuo
  4. extractionextracted with EtOAc
  5. customThe organic layer is separated
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customThe resulting crude product is purified by column chromatography

Sources & evidence

ORD record
ord-f6a5873844b5495d8dc4789e58cd405b
Source dataset
uspto-grants-2014_12
Patent number
US08907097B2

Reaction notes

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