Hydrochloric Acid → 1,2,3,4,5,6-Hexahydro-3,9-dimethylazepino[4,5-b]indole

HRID 1045522

Reaction equation

HRID 1045522 reaction equation
Cl.[C:2]1([CH3:10])[CH:7]=[CH:6][C:5]([NH:8]N)=[CH:4][CH:3]=1.OS(O)(=O)=O.Cl.[OH-].[Na+].[CH3:19][N:20]1[CH2:26][CH2:25][CH2:24][C:23](=O)[CH2:22][CH2:21]1>O1CCOCC1>[CH3:19][N:20]1[CH2:26][CH2:25][C:24]2[C:6]3[CH:7]=[C:2]([CH3:10])[CH:3]=[CH:4][C:5]=3[NH:8][C:23]=2[CH2:22][CH2:21]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 125044-Methylphenylhydrazine monohydrochlorideHCID 14798Sodium HydroxideHCID 2625861-Methylazepan-4-one

Product 1

HCID 685600921,2,3,4,5,6-Hexahydro-3,9-dimethylazepino[4,5-b]indole

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The title compound was prepared by following general procedure 1. p-Tolyl hydrazine hydrochloride (15 g, 94.55 mmol) was taken into 7% H2SO4 in 1,4-dioxane (650 mL), 1-methylazepan-4-one.HCl (15.4 g, 94.55 mmol) was added and stirred at RT for 10 min. The reaction mixture was stirred at 80° C. for 14 h. After completion of the reaction, reaction mass was slowly basified with 50% NaOH solution, extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and evaporated to dryness and purified by column chromatography (silica gel 100-200 mesh; eluent: 10% methanol-DCM) to afford 3,9-dimethyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole (5 g).

Workup

  1. customThe title compound was prepared
  2. stirringThe reaction mixture was stirred at 80° C. for 14 h
  3. customAfter completion of the reaction, reaction mass
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customevaporated to dryness
  7. custompurified by column chromatography (silica gel 100-200 mesh; eluent: 10% methanol-DCM)

Sources & evidence

ORD record
ord-b22701505ed14544a4d9467fc8af3208
Source dataset
uspto-grants-2013_10
Patent number
US08569287B2

Linked notes

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