Sulfuric Acid → 2-Benzyl-2,3,4,5-tetrahydro-1H-pyrido(4,3-b)indole

HRID 522867Notes

Reaction equation

HRID 522867 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:15]1([NH:21]N)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.OS(O)(=O)=O>O1CCOCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2[NH:21][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=3[C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 7516PhenylhydrazineHCID 192201-Benzyl-4-piperidone

Product 1

HCID 2754382-Benzyl-2,3,4,5-tetrahydro-1H-pyrido(4,3-b)indoleYield 95%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1-Benzyl-4-piperidone (1 mmol) was added dropwise to a stirred suspension of phenyl hydrazine (1 equiv.) in a solution of 7% H2SO4 (20 mL) in 1,4-dioxane (20 mL). The reaction mixture was heated at reflux for 18 h then cooled to RT. The solvent was evaporated and the residue recrystallized to afford 2-benzyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (95%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 18 h
  3. customThe solvent was evaporated
  4. customthe residue recrystallized

Sources & evidence

ORD record
ord-e799155e81a64b13a45fb0c2ff99f22d
Source dataset
uspto-grants-2016_05
Patent number
US09334269B2

Reaction notes

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