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

HRID 1401395Notes

Reaction equation

HRID 1401395 reaction equation
Cl.[C:2]1([NH:8]N)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:11][N:12]1[CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]1>CCO>[CH3:11][N:12]1[CH2:17][CH2:16][C:15]2[NH:8][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[C:14]=2[CH2:13]1

Participants

4

Reactant 2

HCID 60962Phenylhydrazine hydrochlorideHCID 122100571-Methylpiperidin-4-one hydrochloride

Product 1

HCID 974242-methyl-2,3,4,5-tetrahydro-1H-pyrido(4,3-b)indole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

Phenyl hydrazine hydrochloride (1 equiv.) and 1-methylpiperidin-4-one hydrochloride (0.76-1.4 equiv.) is dissolved in EtOH and stirred at 80-90° C. overnight. The reaction is monitored by TLC. Upon completion, the reaction mixture is cooled to RT and the solvent is evaporated to dryness. The residue is dissolved in EtOAc and washed with a saturated sodium bicarbonate solution. The organic layer is dried over anhydrous sodium sulfate and evaporated to dryness to afford 2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole.

Workup

  1. temperatureUpon completion, the reaction mixture is cooled to RT
  2. customthe solvent is evaporated to dryness
  3. dissolutionThe residue is dissolved in EtOAc
  4. washwashed with a saturated sodium bicarbonate solution
  5. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-c45cfff1bba24e2e895b02045cbdd40b
Source dataset
uspto-grants-2014_12
Patent number
US08907097B2

Reaction notes

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