tert-Butyl 4-(2-oxo-2,3-dihydro-1H-indol-1-yl)piperidine-1-carboxylate → 1-Piperidin-4-yl-1,3-dihydro-2H-indol-2-one

HRID 967378

Reaktionsgleichung

Reaktionsgleichung von HRID 967378
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:16][C:15]2=[O:23])[CH2:10][CH2:9]1)=O)(C)(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl.C(OCC)C>[NH:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:16][C:15]2=[O:23])[CH2:10][CH2:9]1

Komponenten

4

Edukt 1

HCID 67472855tert-Butyl 4-(2-oxo-2,3-dihydro-1H-indol-1-yl)piperidine-1-carboxylate

Produkt 1

HCID 27611521-Piperidin-4-yl-1,3-dihydro-2H-indol-2-oneAusbeute 150,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 21863450Trifluoroacetic acid methylene chlorideLösungsmittel

Versuchsvorschrift

4-(2-Oxo-2,3-dihydro-indol-1-yl)-piperidine-1-carboxylic acid tert-butyl ester (3.9 g, 12.3 mmol) was set stirring in 30 mL of 1:1 TFA/CH2Cl2. After 45 min the solvent was evaporated under reduced pressure to give a clear purple oil. The oil was brought up in diethyl ether and cooled on ice to give a precipitate. The solid was filtered, washed with ether and air dried to give 4.0 g (100%) of the title compound as a TFA salt. 1H NMR (400 MHz, DMSO-d6): 8.6 (br s, 1H), 7.27 (m, 3H), 7.03 (m, 1H), 4.45 (m, 1H), 3.56 (s, 2H), 3.42 (m, 2H), 3.09 (m, 2H), 2.53 (m, 2H), 1.78 (m, 2H).

Aufarbeitung

  1. customAfter 45 min the solvent was evaporated under reduced pressure
  2. customto give a clear purple oil
  3. temperaturecooled on ice
  4. customto give a precipitate
  5. filtrationThe solid was filtered
  6. washwashed with ether and air
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-cd46555bdbc345a792d754d91f1b4e37
Quelldatensatz
uspto-grants-2005_10
Patentnummer
US06953793B2

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