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

HRID 717793Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 717793
[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

Komponenten

5

Edukt 2

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

Produkt 1

HCID 673765326-bromo-2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indoleAusbeute 69,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1118Sulfuric AcidLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

(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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-c74d18c94e3148159f62eb2521398fad
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09193728B2

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