1-Methyl-4-piperidone → 6-bromo-2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

HRID 717793노트

반응식

HRID 717793 반응식
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[NH:9]N.[CH3:11][N:12]1[CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]1>OS(O)(=O)=O.O1CCOCC1>[Br:1][C:2]1[C:3]2[NH:9][C:15]3[CH2:16][CH2:17][N:12]([CH3:11])[CH2:13][C:14]=3[C:4]=2[CH:5]=[C:6]([CH3:8])[CH:7]=1

참가 물질

5

반응물 2

HCID 740491-Methyl-4-piperidoneHCID 292001(2-Bromo-4-methylphenyl)hydrazine

생성물 1

HCID 673765326-bromo-2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole수율 69.6%

시약·촉매·용매 2

HCID 1118Sulfuric Acid용매HCID 312751,4-Dioxane용매

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온도
80 °C

실험 절차

(2-Bromo-4-methylphenyl)hydrazine (21.5 g, 0.107 mol) and 1-methylpiperidin-4-one (12.5 mL, 0.107 mol) was dissolved in 7% H2SO4 in 1,4-dioxane (150 mL) and stirred at 80° C. for 90 min. The reaction was monitored by TLC. After completion of the reaction, the dioxane was evaporated under reduced pressure, and the residue basified with aq. NaHCO3 solution, and extracted with EtOAc. The organic layer was evaporated under reduced pressure. The crude product was crystallized from hexane and diethyl ether to afford 20.8 g of 6-bromo-2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole. 1H NMR (CDCl3) d (ppm): 10.9 (s, 1H), 7.20 (s, 1H), 7.10 (s, 1H), 3.50 (s, 2H), 2.90-2.80 (t, 2H), 2.70-2.60 (t, 2H), 2.40 (s, 3H), 2.30 (s, 3H).

후처리

  1. customAfter completion of the reaction
  2. customthe dioxane was evaporated under reduced pressure
  3. extractionextracted with EtOAc
  4. customThe organic layer was evaporated under reduced pressure
  5. customThe crude product was crystallized from hexane and diethyl ether

출처 및 근거

ORD 기록
ord-c74d18c94e3148159f62eb2521398fad
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09193728B2

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