Hydrochloric Acid → 9-bromo-6-[(3-chloropropyl)sulfanyl]-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

HRID 1764849Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1764849
Cl.[Br:2][C:3]1[CH:4]=[CH:5][C:6]([S:11][CH2:12][CH2:13][CH2:14][Cl:15])=[C:7]([NH:9]N)[CH:8]=1.O.[NH:17]1[CH2:22][CH2:21][C:20](=O)[CH2:19][CH2:18]1.Cl>CCO>[Br:2][C:3]1[C:8]2[C:19]3[CH2:18][NH:17][CH2:22][CH2:21][C:20]=3[NH:9][C:7]=2[C:6]([S:11][CH2:12][CH2:13][CH2:14][Cl:15])=[CH:5][CH:4]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 21584170Piperidin-4-one hydrateHCID 22735657HCID 22735657, Verbindung

Produkt 1

HCID 160642059-bromo-6-[(3-chloropropyl)sulfanyl]-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indoleAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

1-{5-Bromo-2-[(3-chloropropyl)sulfanyl]phenyl}hydrazine hydrochloride (784 mg, 2.4 mmol) and 4-piperidone monohydrate.HCl (398 mg, 2.6) were dissolved in EtOH (5mL). Conc. Hcl (0.2 mL, 2.4 mmol) were added. The reaction was refluxed for 18 hrs and then cooled to rt. The ppt was collected by filtration and the residue was washed with EtOH (3mL). 9-bromo-6-[(3-chloropropyl)sulfanyl]-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole hydrochloroide (500.4 mg, 58%) was isolated as a white powder. 1H NMR (CD3OD, 300 Mhz) δ7.18 (d, 1H, 8.0 Hz), 7.12 (d, 1H, 8.0 Hz), 4.73 (s, 2H), 3.64 (t, 2H, 6.6 Hz), 3.58 (t, 2H, 6.3 Hz), 3.16 (t, 2H, 6.3 Hz), 3.02 (t, 2H, 6.6 Hz), 1.87-1.96 (m, 2H) ppm.

Aufarbeitung

  1. additionConc. Hcl (0.2 mL, 2.4 mmol) were added
  2. temperatureThe reaction was refluxed for 18 hrs
  3. filtrationThe ppt was collected by filtration
  4. washthe residue was washed with EtOH (3mL)

Quellen und Nachweise

ORD-Eintrag
ord-aa95bae0dcbf4865b31b541e766bcfe2
Quelldatensatz
uspto-grants-2007_06
Patentnummer
USRE039679E1

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