Phenylhydrazine hydrochloride → 2-Ethyl-2,3,4,5-tetrahydro-1H-pyrido(4,3-b)indole

HRID 1401397Notes

Reaction equation

HRID 1401397 reaction equation
Cl.[C:2]1([NH:8]N)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH2:11]([N:13]1[CH2:18][CH2:17][C:16](=O)[CH2:15][CH2:14]1)[CH3:12]>CCO>[CH2:11]([N:13]1[CH2:18][CH2:17][C:16]2[NH:8][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[C:15]=2[CH2:14]1)[CH3:12]

Participants

4

Reactant 2

HCID 60962Phenylhydrazine hydrochlorideHCID 123199151-Ethylpiperidin-4-one--hydrogen chloride (1/1)

Product 1

HCID 5888242-Ethyl-2,3,4,5-tetrahydro-1H-pyrido(4,3-b)indole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of phenylhydrazine hydrochloride (1 equiv.) in EtOH is added 1-ethylpiperidin-4-one hydrochloride (0.76-1.4 equiv.) and the reaction mixture is heated at 80° C. for 16 h. After completion of the reaction, e.g., as monitored by liquid chromatography-mass spectrometry (LCMS), the reaction mixture is concentrated to dryness and basified with aq. saturated NaHCO3 and extracted in EtOAc. The organic layer is separated, dried over sodium sulfate and concentrated to obtain 2-ethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole.

Workup

  1. customAfter completion of the reaction, e.g.
  2. concentrationthe reaction mixture is concentrated to dryness
  3. extractionextracted in EtOAc
  4. customThe organic layer is separated
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5d61ed66498243dea5c9d61675d7d74d
Source dataset
uspto-grants-2014_12
Patent number
US08907097B2

Reaction notes

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