Sulfuric Acid → 6-Chloro-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole
Reaktionsgleichung
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9]N.OS(O)(=O)=O.[CH3:16][N:17]1[CH2:22][CH2:21][C:20](=O)[CH2:19][CH2:18]1>O1CCOCC1>[Cl:2][C:3]1[C:4]2[NH:9][C:20]3[CH2:21][CH2:22][N:17]([CH3:16])[CH2:18][C:19]=3[C:5]=2[CH:6]=[CH:7][CH:8]=1Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 80 °C
Versuchsvorschrift
To a suspension of 2-chlorophenyl hydrazine hydrochloride (19.7 g, 0.110 mol) in dioxane (190 mL) at RT was added conc. H2SO4 (8 mL, 0.150 mol) dropwise and the reaction mixture was stirred for 10 min. To this was added N-methyl-4-piperidone (17.53 g, 0.154 mol) and the reaction mixture was stirred at RT for 20 min, then heated at 80° C. for 4 h. The reaction was monitored by TLC. The solvent was evaporated and pH adjusted to pH 8-9 with saturated sodium bicarbonate solution. The product was extracted with EtOAc (3×300 mL). The combined organic layer was washed with water and brine, dried over sodium sulfate, and concentrated under vacuum. The crude product was purified by recrystallization (Ether/Hexane). The filtered solid was dried in vacuo to obtain 7.5 g of product as a brown solid. 1H NMR (CDCl3, freebase) d (ppm): 8.10 (bs, 1H), 7.30 (d, 1H), 7.10 (d, 1H), 7.0 (t, 1H), 3.62 (s, 2H), 2.90 (m, 2H), 2.82 (m, 2H), 2.38 (s, 3H).
Aufarbeitung
- stirringthe reaction mixture was stirred at RT for 20 min
- customThe solvent was evaporated
- extractionThe product was extracted with EtOAc (3×300 mL)
- washThe combined organic layer was washed with water and brine
- dry with materialdried over sodium sulfate
- concentrationconcentrated under vacuum
- customThe crude product was purified by recrystallization (Ether/Hexane)
- customThe filtered solid was dried in vacuo
Quellen und Nachweise
- ORD-Eintrag
- ord-24ea880e26d44712858cc15187d6e6f6
- Quelldatensatz
- uspto-grants-2015_11
- Patentnummer
- US09193728B2
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