Phenylhydrazine hydrochloride → 2,3,4,5-Tetrahydro-1H-pyrido[4,3-b]indole hydrochloride
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]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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
- temperatureat reflux overnight
- filtrationThe resulting solid is filtered off
- 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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