Piperonylamine → 8-Methoxy-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

HRID 2236108Notes

Reaction equation

HRID 2236108 reaction equation
Cl.O.[NH:3]1[CH2:8][CH2:7][C:6](=O)[CH2:5][CH2:4]1.Cl.[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19]N)=[CH:15][CH:14]=1>C(O)C>[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]2[NH:19][C:6]3[CH2:5][CH2:4][NH:3][CH2:8][C:7]=3[C:15]=2[CH:14]=1

Participants

4

Reactant 2

HCID 2723901PiperonylamineHCID 27239044-Methoxyphenylhydrazine hydrochloride

Product 1

HCID 4247018-Methoxy-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 4-piperidone monohydrate hydrochloride (1.0 g, 6.5 mmol) and 4-methoxyphenylhydrazine hydrochloride (1.14 g, 6.5 mmol) in ethanol (17 ml) is kept stirring at reflux overnight. The resulting solid is filtered off and washed with diethyl ether to afford crude sub-title compound, which is used without further purification: tR (LC-1) 0.38; ESI-MS (positive ion): m/z 203.19 [M+H]+ (calcd 202.25 for C12H14N2O).

Workup

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

Sources & evidence

ORD record
ord-20d12c8a9c654fc2ac752bec5935fac4
Source dataset
uspto-grants-2010_05
Patent number
US07714132B2

Reaction notes

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