Hydrochloric Acid → HCID 17749802, Verbindung

HRID 1093568

Reaktionsgleichung

Reaktionsgleichung von HRID 1093568
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([S:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[Cl:21])[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>O1CCOCC1>[ClH:21].[Cl:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[S:14][CH:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 58724129Tert-butyl 4-(2-chlorophenylthio)piperidine-1-carboxylate

Produkt 1

HCID 17749802HCID 17749802, VerbindungAusbeute 232,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a stirred solution of 2-chlorobenzenethiol (2.5 g, 0.017 mole) in DMF (20 mL) was added cesium carbonate (6.77 g, 0.0208 mole), followed by 4-methanesulfonyloxy-piperidine-1-carboxylic acid tert-butyl ester (4.8 g, 0.0173 mole). The reaction mixture was heated at 80° C. overnight. The mixture was then diluted with cold water and the product was extracted with ethyl acetate. The ethyl acetate layer was washed with brine solution, dried over sodium sulfate and concentrated under reduced pressure to afford 4.64 g (82%) of 4-(2-chloro-phenylsulfanyl)-piperidine-1-carboxylic acid tert-butyl ester. LCMS: 328.11 (M+1)+, 95.12%. A solution of 4-(2-chloro-phenylsulfanyl)-piperidine-1-carboxylic acid tert-butyl ester (4 g, 0.0122 mole) in dioxane.HCl (7 mL) was stirred at ambient temperature for 30 minutes. The reaction mixture was then concentrated under reduced pressure and the resulting residue was washed with hexane twice to afford 3.75 g (99%) of 4-(2-chloro-phenylsulfanyl)-piperidine hydrochloride. LCMS: 228.05 (M+1)+, 92.02%.

Aufarbeitung

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. washthe resulting residue was washed with hexane twice

Quellen und Nachweise

ORD-Eintrag
ord-aae78e48e18d4b1691ee0c273e56125a
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08129376B2

Verknüpfte Notizen

Wird geladen…