4-Methylphenylhydrazine monohydrochloride → 2-ethyl-8-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

HRID 1401399Notes

Reaction equation

HRID 1401399 reaction equation
Cl.[C:2]1([CH3:10])[CH:7]=[CH:6][C:5]([NH:8]N)=[CH:4][CH:3]=1.Cl.[CH2:12]([N:14]1[CH2:19][CH2:18][C:17](=O)[CH2:16][CH2:15]1)[CH3:13]>CCO>[CH2:12]([N:14]1[CH2:19][CH2:18][C:17]2[NH:8][C:5]3[CH:4]=[CH:3][C:2]([CH3:10])=[CH:7][C:6]=3[C:16]=2[CH2:15]1)[CH3:13]

Participants

4

Reactant 2

HCID 125044-Methylphenylhydrazine monohydrochlorideHCID 123199151-Ethylpiperidin-4-one--hydrogen chloride (1/1)

Product 1

HCID 594550662-ethyl-8-methyl-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 p-tolylhydrazine hydrochloride (1 equiv.) in EtOH is added 1-ethylpiperidin-4-one hydrochloride (0.76-1.4 equiv.) and the contents are heated at 80° C. for 16 h. After completion of the reaction, as monitored by LCMS, the reaction mixture is concentrated to dryness and basified with aq. saturated NaHCO3. The reaction product is extracted with EtOAc and the organic layer is separated, dried over sodium sulfate and concentrated to obtain 2-ethyl-8-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole.

Workup

  1. customAfter completion of the reaction
  2. concentrationthe reaction mixture is concentrated to dryness
  3. extractionThe reaction product is extracted with EtOAc
  4. customthe organic layer is separated
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0f9a64b3e044477f966a8c7b708f9d2c
Source dataset
uspto-grants-2014_12
Patent number
US08907097B2

Reaction notes

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