Maleic Anhydride → (1S)-2-(1-Cyclohexylpiperidin-4-yl)-1-methyl-3-oxo-2,3-dihydro-1H-isoindole-4-carboxylic acid

HRID 1618115Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1618115
[CH:1]1([N:7]2[CH2:12][CH2:11][CH:10]([NH:13][C@H:14]([C:16]3O[CH:18]=[CH:19][CH:20]=3)[CH3:15])[CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:21]1(=[O:27])[O:26][C:24](=[O:25])[CH:23]=[CH:22]1>C1(C)C=CC=CC=1>[CH:1]1([N:7]2[CH2:8][CH2:9][CH:10]([N:13]3[C:24](=[O:25])[C:23]4[C:22]([C:21]([OH:26])=[O:27])=[CH:18][CH:19]=[CH:20][C:16]=4[C@@H:14]3[CH3:15])[CH2:11][CH2:12]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

4

Edukt 2

HCID 7923Maleic AnhydrideHCID 671921261-cyclohexyl-N-[(1S)-1-(furan-2-yl)ethyl]piperidin-4-amine

Produkt 1

HCID 67191867(1S)-2-(1-Cyclohexylpiperidin-4-yl)-1-methyl-3-oxo-2,3-dihydro-1H-isoindole-4-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

1-Cyclohexyl-N-[(1S)-1-(furan-2-yl)ethyl]piperidin-4-amine (0.3 gr, 1.08 mmol) and maleic anhydride (0.13 gr, 1.3 mmol) in toluene (10 mL) were stirred at reflux for 16 hours. Solvent was evaporated and the residue was dissolved in aqueous 37% hydrochloric acid (5 mL) and stirred at 100° C. for 2 hours. Volatiles were evaporated affording crude title product that was used for the next step without further purification

Aufarbeitung

  1. temperatureat reflux for 16 hours
  2. customSolvent was evaporated
  3. dissolutionthe residue was dissolved in aqueous 37% hydrochloric acid (5 mL)
  4. customVolatiles were evaporated

Quellen und Nachweise

ORD-Eintrag
ord-f579d8ef94394998baa2c9e63caaeb02
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765972B2

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