Phthalimide → (5)-2-(1-(4-(Methoxy)phenyl)ethyl)isoindoline-1,3-dione

HRID 709434

Reaktionsgleichung

Reaktionsgleichung von HRID 709434
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([C@@H:20](N)[CH3:21])=[CH:16][CH:15]=1.C([O-])([O-])=O.[K+].[K+]>CCCCO>[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([C@@H:20]([N:5]2[C:1](=[O:11])[C:2]3[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:4]2=[O:6])[CH3:21])=[CH:16][CH:15]=1

Komponenten

5

Edukt 3

HCID 6809PhthalimideHCID 11430Potassium CarbonateHCID 793467(S)-1-(4-Methoxyphenyl)ethylamine

Produkt 1

HCID 101694173(5)-2-(1-(4-(Methoxy)phenyl)ethyl)isoindoline-1,3-dioneAusbeute 64,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

To phthalimide (1.3 g, 0.0088 mol) in a 2-5 mL microwave vial was added (S)-1-(4-methoxyphenyl)ethan-1-amine (2.20 mL, 0.015 mol) and K2CO3 (1.2 g, 0.0087 mol). The reaction mixture capped and heated at 160° C. for 2 minutes. The resulting crude solid was suspended in n-BuOH and was filtered. The filtrate was put aside. The solid was washed with H2O and the filtrate was discarded. The solid was washed with CH2Cl2 and the resulting filtrate was partitioned with H2O. The organics (n-BuOH and CH2Cl2 layer) were combined and concentrated. The crude residue was purified by silica gel column chromatography using CH2Cl2 as eluent to yield 1.6 g (64%) of the title compound. LC/MS: m/z (ES+) 282 (M+H)+.

Aufarbeitung

  1. customThe reaction mixture capped
  2. filtrationwas filtered
  3. washThe solid was washed with H2O
  4. washThe solid was washed with CH2Cl2
  5. customthe resulting filtrate was partitioned with H2O
  6. concentrationconcentrated
  7. customThe crude residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c18f34cedcee43ec9062a99d9d271c44
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181200B2

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