Triethylamine → 2-(4-(1,3-Dioxoisoindolin-2-yloxy)piperidin-1-yl)-2-(4-(trifluoromethoxy)phenyl)acetonitrile

HRID 1895943Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1895943
[F:1][C:2]([F:13])([F:12])[O:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1.P([C:22]#[N:23])(=O)(OCC)OCC.Cl.[NH:25]1[CH2:30][CH2:29][CH:28]([O:31][N:32]2[C:40](=[O:41])[C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[C:33]2=[O:42])[CH2:27][CH2:26]1.C(N(CC)CC)C>O1CCCC1>[O:41]=[C:40]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:33](=[O:42])[N:32]1[O:31][CH:28]1[CH2:29][CH2:30][N:25]([CH:8]([C:7]2[CH:10]=[CH:11][C:4]([O:3][C:2]([F:13])([F:12])[F:1])=[CH:5][CH:6]=2)[C:22]#[N:23])[CH2:26][CH2:27]1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 69573p-(Trifluoromethoxy)benzaldehydeHCID 76257Diethyl cyanophosphonateHCID 217515372-(Piperidin-4-yloxy)isoindoline-1,3-dione hydrochloride

Produkt 1

HCID 671184582-(4-(1,3-Dioxoisoindolin-2-yloxy)piperidin-1-yl)-2-(4-(trifluoromethoxy)phenyl)acetonitrileAusbeute 29,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

4-(Trifluoromethoxy)benzaldehyde (0.342 ml, 2.39 mmol) was added to a solution of diethyl phosphorocyanidate (0.363 ml, 2.39 mmol) in tetrahydrofuran (12 ml) and stirred at room temperature for 10 minutes. A suspension of 2-(piperidin-4-yloxy)isoindoline-1,3-dione hydrochloride (564 mg, 2.00 mmol) and triethylamine (0.332 ml, 2.39 mmol) in tetrahydrofuran (6 ml) was added to the reaction mixture, and the whole was stirred at room temperature for 24 hours and at 60° C. for 17 hours. The reaction mixture was concentrated in vacuo and the residue was purified by column chromatography (ethyl acetate/hexane: 5/95 to 25/75) to give 2-(4-(1,3-dioxoisoindolin-2-yloxy)piperidin-1-yl)-2-(4-(trifluoromethoxy)phenyl)acetonitrile (261 mg, 22%).

Aufarbeitung

  1. additionwas added to the reaction mixture
  2. stirringthe whole was stirred at room temperature for 24 hours and at 60° C. for 17 hours
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customthe residue was purified by column chromatography (ethyl acetate/hexane: 5/95 to 25/75)

Quellen und Nachweise

ORD-Eintrag
ord-587d14d2674f45499c15c61af40faecb
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08518934B2

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