Hydrochloric Acid → 1253640-41-3

HRID 1773284Notes

Reaction equation

HRID 1773284 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10]N.[CH3:12][N:13]1[CH2:18][CH2:17][C:16](=O)[CH2:15][CH2:14]1.Cl>C(O)C>[CH3:2][O:3][C:4]1[C:5]2[NH:10][C:16]3[CH2:17][CH2:18][N:13]([CH3:12])[CH2:14][C:15]=3[C:6]=2[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 740491-Methyl-4-piperidoneHCID 28494452-Methoxyphenylhydrazine Hydrochloride

Product 1

HCID 545884621253640-41-3Yield 30.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of (2-methoxyphenyl)hydrazine hydrochloride (5 g, 0.0286 mol) and 1-methyl-4-piperidone (2.83 mL, 0.0229 mol) in ethanol (50 mL) was added ethanolic hydrochloric acid (5 mL). The reaction mixture was heated at 80° C. for 2 h. After completion, the reaction mixture was cooled to RT and solvent removed under reduced pressure. The residue was basified with 10% sodium hydroxide solution and extracted with EtOAc (3×100 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford crude material, which was purified by silica gel column chromatography (6% MeOH:DCM) to yield 6-methoxy-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (1.5 g, 24% yield).

Workup

  1. temperatureAfter completion, the reaction mixture was cooled to RT
  2. customsolvent removed under reduced pressure
  3. extractionextracted with EtOAc (3×100 mL)
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto afford crude material, which
  7. customwas purified by silica gel column chromatography (6% MeOH:DCM)

Sources & evidence

ORD record
ord-03f710c3dd7146c298834a98addd6d07
Source dataset
uspto-grants-2016_02
Patent number
US09255094B2

Reaction notes

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