Hydrochloric Acid → 5-bromo-2-methyl-3-(piperidin-4-ylthio)-1H-indole

HRID 36886

Reaktionsgleichung

Reaktionsgleichung von HRID 36886
Cl.[Br:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9]N)=[CH:5][CH:4]=1.O=[C:12]([CH3:28])[CH2:13][S:14][CH:15]1[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][CH2:16]1.Cl.CCOCC>C(O)(C)C>[Br:2][C:3]1[CH:8]=[C:7]2[C:6](=[CH:5][CH:4]=1)[NH:9][C:12]([CH3:28])=[C:13]2[S:14][CH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 121574-Bromophenylhydrazine hydrochlorideHCID 199366031,1-Dimethylethyl 4-[(2-oxopropyl)thio]piperidine-1-carboxylate

Produkt 1

HCID 99053425-bromo-2-methyl-3-(piperidin-4-ylthio)-1H-indoleAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

4-Bromophenylhydrazine hydrochloride (11.5 g) is solubilized in a solution of 1,1-dimethylethyl 4-[(2-oxopropyl)thio]piperidine-1-carboxylate (14 g, prepared in Example 11) in isopropanol (100 ml) under nitrogen. The solution is cooled to 0° C. and saturated with gaseous hydrogen chloride. After 4 hours at room temperature, the precipitate is filtered off, taken up in sodium hydroxide and extracted with ether and then with methylene chloride. The organic phases are combined, dried over sodium sulfate and concentrated. The solid obtained is taken up in the minimum amount of ether and recrystallized from xylene to give 5-bromo-2-methyl-3-(piperidin-4-ylthio)-1H-indole (9.5 g).

Aufarbeitung

  1. filtrationthe precipitate is filtered off
  2. extractionextracted with ether
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe solid obtained
  6. customrecrystallized from xylene

Quellen und Nachweise

ORD-Eintrag
ord-2f1d1b5dffd3455f9f2cc1fcb715958f
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05418242

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