Phenylhydrazine hydrochloride → 2,3,4,5-Tetrahydro-1H-pyrido[4,3-b]indole hydrochloride

HRID 2236094Notes

Reaction equation

HRID 2236094 reaction equation
[ClH:1].O.[NH:3]1[CH2:8][CH2:7][C:6](=O)[CH2:5][CH2:4]1.Cl.[C:11]1([NH:17]N)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(O)C>[ClH:1].[CH2:4]1[C:5]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[NH:17][C:6]=2[CH2:7][CH2:8][NH:3]1

Participants

4

Reactant 2

HCID 60962Phenylhydrazine hydrochlorideHCID 2723901Piperonylamine

Product 1

HCID 115720112,3,4,5-Tetrahydro-1H-pyrido[4,3-b]indole hydrochlorideYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Piperidone monohydrate hydrochloride (10 g, 65.1 mmol) and phenylhydrazine hydrochloride (9.4 g, 65.1 mmol) are suspended in ethanol (200 ml) and stirred at reflux overnight. The resulting solid is filtered off and washed with diethyl ether to afford pure sub-title compound (11.9 g) in 88% yield. tR (LC-2) 0.89; ESI-MS (positive ion): m/z 173.34 [M+H]+ (calcd 172.23 for C11H12N2).

Workup

  1. temperatureat reflux overnight
  2. filtrationThe resulting solid is filtered off
  3. washwashed with diethyl ether

Sources & evidence

ORD record
ord-96e7a1b6446b460c818ddf17c8a17d1e
Source dataset
uspto-grants-2010_05
Patent number
US07714132B2

Reaction notes

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