Hydrochloric Acid → 2,6-Dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

HRID 1400335Notes

Reaction equation

HRID 1400335 reaction equation
Cl.[CH3:2][N:3]1[CH2:8][CH2:7][C:6](=O)[CH2:5][CH2:4]1.Cl.[CH3:11][CH2:12]O>>[CH3:2][N:3]1[CH2:8][CH2:7][C:6]2[NH:3][C:4]3[C:12]([CH3:11])=[CH:8][CH:7]=[CH:6][C:5]=3[C:5]=2[CH2:4]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 122100571-Methylpiperidin-4-one hydrochloride

Product 1

HCID 5939582,6-Dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

Conditions

Temperature
80 °C

Procedure

O-Tolyl hydrazine hydrochloride (1 equiv.) is taken in EtOH. 1-Methylpiperidin-4-one hydrochloride (0.76-1.4 equiv.) and ethanolic HCl is added (pH acidic) and the contents are stirred at 80° C. for 5 h. The reaction is monitored by TLC. After completion of the reaction, the reaction mixture is concentrated. The residue is dissolved in aq NaHCO3 solution and extracted with EtOAc. The organic layer is dried over anhydrous sodium sulfate and evaporated under reduced pressure to afford 2,6-dimethyl-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. dissolutionThe residue is dissolved in aq NaHCO3 solution
  4. extractionextracted with EtOAc
  5. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-1294a0daaf8a4a30bc4ee11a12566583
Source dataset
uspto-grants-2014_12
Patent number
US08906925B2

Reaction notes

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