2-[2-(oxiran-2-yl)ethyl]-2,3-dihydro-1H-isoindole-1,3-dione → 2-(4-(4-(2,3-Dichlorophenyl)-piperazin-1-yl)-3-hydroxybutyl)-isoindoline-1,3-dione

HRID 404579

Reaktionsgleichung

Reaktionsgleichung von HRID 404579
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.[O:15]1[CH2:17][CH:16]1[CH2:18][CH2:19][N:20]1[C:28](=[O:29])[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]1=[O:30]>>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:17][CH:16]([OH:15])[CH2:18][CH2:19][N:20]2[C:28](=[O:29])[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:21]2=[O:30])[CH2:11][CH2:10]1

Komponenten

3

Edukt 2

HCID 3394332-[2-(oxiran-2-yl)ethyl]-2,3-dihydro-1H-isoindole-1,3-dioneHCID 8518331-(2,3-Dichlorophenyl)piperazine

Produkt 1

HCID 685058792-(4-(4-(2,3-Dichlorophenyl)-piperazin-1-yl)-3-hydroxybutyl)-isoindoline-1,3-dione

Versuchsvorschrift

A sample of 2.1 g (9.0 mmol) 1-(2,3-dichlorophenyl)-piperazine in 40 mL 2-PrOH was reacted in the microwave (pressure vessel, Pmax 150 W, cooling, 90° C., 20 min) with 2.0 g (9.0 mmol) 25. The solvent was removed in vacuo and the foamy residue was washed with 10 mL 2-PrOH. Yield: 2.96 g (73%). 1H NMR (CDCl3): δ 1.79 (m, 2H), 2.42 (m, 2H), 2.56 (s, 2H), 2.79 (m, 2H), 3.02 (s, 4H), 3.60 (s, 1H), 3.74-3.83 (m, 3H), 6.90 (m, 1H), 7.06-7.11 (m, 2H), 7.67 (m, 2H), 7.81 (m, 2H). 13C NMR (CDCl3): δ 33.9, 35.3, 51.4, 53.4, 63.8, 64.5, 118.2, 122.7, 124.1, 127.0, 131.6, 133.4, 133.4, 150.4, 167.7.

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. washthe foamy residue was washed with 10 mL 2-PrOH

Quellen und Nachweise

ORD-Eintrag
ord-403dd16b5e6a4444966c969eb59d0686
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748608B2

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