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

HRID 1045522

反応式

HRID 1045522 の反応式
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

参加物

7

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-b22701505ed14544a4d9467fc8af3208
出典データセット
uspto-grants-2013_10
特許番号
US08569287B2

関連ノート

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