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

HRID 1401396Notes

Reaction equation

HRID 1401396 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>C(O)C>[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)indoleYield 53.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

Phenyl hydrazine hydrochloride (5 g, 34.57 mmol) and 1-methylpiperidin-4-one hydrochloride (4.5 g, 30.1 mmol, 1 eq.) was dissolved in of ethanol (150 mL) and stirred at 80-90° C. for overnight. The reaction was monitored by TLC. The mixture was cooled to RT, solvent was concentrated under reduced pressure. The residue was dissolved in EtOAc, washed with saturated sodium bicarbonate solution. Organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford 3.0 g of 2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole. 1H NMR (CDCl3, free base) δ (ppm) 8.0 (bs, 1H), 7.4 (d, 1H), 7.35 (d, 1H), 7.20-7.0 (m, 2H), 3.7 (s, 2H), 2.9 (s, 4H), 2.6 (s, 3H).

Workup

  1. temperatureThe mixture was cooled to RT
  2. concentrationsolvent was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed with saturated sodium bicarbonate solution
  5. dry with materialOrganic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-14fb112f5344431184bdb9786f475c4b
Source dataset
uspto-grants-2014_12
Patent number
US08907097B2

Reaction notes

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