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Potassium Hydroxide → HCID 46224945, Verbindung

HRID 1401641
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1401641
[CH3:1][N:2]1[CH2:25][CH2:24][C:5]2[N:6]([CH:14]([CH3:23])[CH:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)O)[C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]=2[CH2:3]1.S(Cl)(Cl)=O.[OH-].[K+]>C(Cl)Cl.CN(C=O)C.CN1C(=O)CCC1.O>[CH3:1][N:2]1[CH2:25][CH2:24][C:5]2[N:6](/[C:14](/[CH3:23])=[CH:15]\[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]=2[CH2:3]1.[CH3:1][N:2]1[CH2:25][CH2:24][C:5]2[N:6](/[C:14](/[CH3:23])=[CH:15]/[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]=2[CH2:3]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 3

HCID 14797Potassium HydroxideHCID 24386Thionyl ChlorideHCID 59455003HCID 59455003, Verbindung

Produkt 2

HCID 46224945HCID 46224945, VerbindungHCID 59455062HCID 59455062, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 6228
Dimethylformamide
Katalysator
HCID 962WaterLösungsmittel
HCID 6344DichloromethaneLösungsmittel
HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

A solution of 2-(2,8-dimethyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl)-1-phenyl-propan-1-ol (100 mg, 0.29 mmol) in DCM (5 mL) and DMF (2 drops) was stirred at 0-10° C. Thionyl chloride (0.8 mL, 11.02 mmol) was added and the reaction mixture stirred at RT for 2 h. The solvent was removed under vacuum to obtain the crude as a dark brown solid, which was dissolved in NMP (2 mL) and stirred for 5 min. Powdered KOH (167 mg, 2.99 mmol) was added to the reaction mixture and the contents heated at 85° C. for 45 min. After completion of reaction, the reaction mixture was poured in water and the desired compound extracted with EtOAc (3×100 mL). The organic layer was dried over anhydrous sodium sulfate, concentrated under vacuum to obtain the crude product (40 mg) which was purified by reverse phase HPLC to yield (Z)-2,8-Dimethyl-5-(1-methyl-2-phenyl-vinyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (10 mg) and (E)-2,8-Dimethyl-5-(1-methyl-2-phenyl-vinyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (12 mg) which were converted to their respective HCl salts. 1H NMR (CDCl3, free base) δ (ppm): 7.40 (m, 3H), 7.30-7.20 (m, 4H), 6.98 (d, 1H), 6.60 (s, 1H), 3.76 (s, 2H), 2.60 (s, 3H), 2.30 (s, 3H).

Aufarbeitung

  1. customThe solvent was removed under vacuum
  2. customto obtain the crude as a dark brown solid, which
  3. stirringstirred for 5 min
  4. temperaturethe contents heated at 85° C. for 45 min
  5. customAfter completion of reaction
  6. extractionthe desired compound extracted with EtOAc (3×100 mL)
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. concentrationconcentrated under vacuum
  9. customto obtain the crude product (40 mg) which
  10. customwas purified by reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-55ae362c4afb4099a5eaa1da312967c9
Quelldatensatz
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08907097B2

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