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

HRID 1401410노트

반응식

HRID 1401410 반응식
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>OS(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

참가 물질

5

반응물 2

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

생성물 1

HCID 594549332-methyl-8-trifluoromethoxy-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole수율 76.2%

시약·촉매·용매 2

HCID 1118Sulfuric Acid용매HCID 312751,4-Dioxane용매

반응 조건

온도
80 °C

실험 절차

(4-(Trifluoromethoxy)phenyl)hydrazine hydrochloride (1 g, 4.37 mmol) was dissolved in 7% H2SO4 in 1,4-dioxane (50 mL), 1-methylpiperidin-4-one hydrochloride (0.65 g, 4.37 mmol) was added and stirred at 80° C. for 6 h. Reaction was monitored by TLC & LCMS. After completion of the reaction, reaction mixture was concentrated under vacuum and slowly quenched with aq. NaHCO3 solution, extracted with EtOAc. Organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure and purified by column chromatography to afford 0.9 g of 2-methyl-8-(trifluoromethoxy)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole. 1H NMR (CDCl3, free base) δ (ppm) 7.9 (bs, 1H), 7.3-7.2 (m, 2H), 7.1-6.9 (d, 1H), 3.7 (s, 2H), 2.9-2.8 (m, 4H), 2.6 (s, 3H).

후처리

  1. customReaction
  2. customAfter completion of the reaction, reaction mixture
  3. concentrationwas concentrated under vacuum
  4. customslowly quenched with aq. NaHCO3 solution
  5. extractionextracted with EtOAc
  6. dry with materialOrganic layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. custompurified by column chromatography

출처 및 근거

ORD 기록
ord-d07e2f6104d4425d9120b471521a8845
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08907097B2

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