1-Benzyloxycarbonyl-4-(2-methylsulfinylphenyl)piperidine → 4-(2-(Methylsulfinyl)phenyl)piperidine

HRID 2256050Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2256050
C(OC([N:11]1[CH2:16][CH2:15][CH:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[S:23]([CH3:25])=[O:24])[CH2:13][CH2:12]1)=O)C1C=CC=CC=1>FC(F)(F)C(O)=O>[CH3:25][S:23]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[CH:14]1[CH2:15][CH2:16][NH:11][CH2:12][CH2:13]1)=[O:24]

Komponenten

3

Edukt 1

HCID 226222471-Benzyloxycarbonyl-4-(2-methylsulfinylphenyl)piperidine

Produkt 1

HCID 187003874-(2-(Methylsulfinyl)phenyl)piperidineAusbeute 83,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

A solution of 1-benzyloxycarbonyl-4-(2-methylsulfinylphenyl)piperidine (1.66 g) in 8 mL of trifluoroacetic acid was heated to reflux for 45 minutes. At the end of this period, the reaction mixture was evaporated and the residue was treated with toluene. Upon evaporating the solvent, the residue was treated with an additional portion of toluene and the process was repeated. The final residue was dried under reduced pressure and purified by chromatography; elution with dichloromethane:methanol:triethylamine (19:1:1) afforded the named product (0.87 g); MS: 224; NMR: 1.6-2.4 (m, 4), 2.7 (two peaks, 3), 2.9-3.2 (m, 3), 3.3-3.5 (m, 2), 5.3-5.7 (br, 1), 7.4-7.5 (m, 3), 7.9-8.0 (m, 1).

Aufarbeitung

  1. temperatureto reflux for 45 minutes
  2. customAt the end of this period, the reaction mixture was evaporated
  3. additionthe residue was treated with toluene
  4. customUpon evaporating the solvent
  5. additionthe residue was treated with an additional portion of toluene
  6. dry with materialThe final residue was dried under reduced pressure
  7. custompurified by chromatography
  8. washelution with dichloromethane:methanol:triethylamine (19:1:1)

Quellen und Nachweise

ORD-Eintrag
ord-c30efc5ee7bf4ce7b3bcb7f8bee00e91
Quelldatensatz
uspto-grants-1997_08
Patentnummer
US05654299

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