4-(Trifluoromethoxy)phenylhydrazine hydrochloride → 2-methyl-8-trifluoromethoxy-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

HRID 1400333ノート

反応式

HRID 1400333 の反応式
Cl.[F:2][C:3]([F:14])([F:13])[O:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11]N)=[CH:7][CH:6]=1.Cl.[CH3:16][N:17]1[CH2:22][CH2:21][C:20](=O)[CH2:19][CH2:18]1>S(=O)(=O)(O)O.O1CCOCC1>[CH3:16][N:17]1[CH2:22][CH2:21][C:20]2[NH:11][C:8]3[CH:7]=[CH:6][C:5]([O:4][C:3]([F:14])([F:13])[F:2])=[CH:10][C:9]=3[C:19]=2[CH2:18]1

参加物

5

反応物 2

HCID 27773284-(Trifluoromethoxy)phenylhydrazine hydrochlorideHCID 122100571-Methylpiperidin-4-one hydrochloride

生成物 1

HCID 594549332-methyl-8-trifluoromethoxy-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

試薬・触媒・溶媒 2

HCID 1118Sulfuric Acid溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

(4-(Trifluoromethoxy)phenyl)hydrazine hydrochloride (1 equiv.) is taken in 7% sulfuric acid in 1,4-dioxane. 1-Methylpiperidin-4-one hydrochloride (0.76-1.4 equiv.) is added and the mixture is stirred at 80° C. for 6 h. The reaction is monitored by TLC and LCMS. After completion of the reaction, the reaction mixture is concentrated, then slowly quenched with aq. NaHCO3 solution and extracted with EtOAc. The organic layer is dried over anhydrous sodium sulfate, evaporated to dryness and purified by column chromatography to afford 2-methyl-8-(trifluoromethoxy)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole.

後処理

  1. customAfter completion of the reaction
  2. concentrationthe reaction mixture is concentrated
  3. customslowly quenched with aq. NaHCO3 solution
  4. extractionextracted with EtOAc
  5. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  6. customevaporated to dryness
  7. custompurified by column chromatography

出典と根拠

ORDレコード
ord-fb4e43e11b384b9a841c6f9aa906b4b2
出典データセット
uspto-grants-2014_12
特許番号
US08906925B2

反応ノート

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