Reaktionsgleichung
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][CH:8]([C:11]2[C:15]3[CH:16]=[CH:17][C:18]([F:20])=[CH:19][C:14]=3[O:13][N:12]=2)[CH2:7][CH2:6]1.[C@@H:21]12[C:30](=O)[O:29][C:27](=[O:28])[C@@H:22]1[CH2:23][CH2:24][CH2:25][CH2:26]2.[ClH:32]>N1C=CC=CC=1.C(O)C>[ClH:32].[F:20][C:18]1[CH:17]=[CH:16][C:15]2[C:11]([CH:8]3[CH2:9][CH2:10][N:5]([CH2:4][CH2:3][CH2:2][N:1]4[C:27](=[O:28])[C@H:22]5[C@H:21]([CH2:26][CH2:25][CH2:24][CH2:23]5)[C:30]4=[O:29])[CH2:6][CH2:7]3)=[N:12][O:13][C:14]=2[CH:19]=1Komponenten
6
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
A mixture of 1-(3-aminopropyl)-4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine (3.01 g, 10.8 mmol) and cis-1,2-cyclohexane-dicarboxylic anhydride (1.9 g, 12.3 mmol) in dry pyridine (30 ml) was heated at reflux for 16 hours. The dark brown solution was concentrated to dryness on a rotary evaporator. The crude residue was purified twice by flash chromatography over a silica gel column. The pure product thus obtained weighed 2.5 g (67%). This was converted to the hydrochloride salt by treatment with HCl in ethanol (50 ml). The cis-2-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]propyl]-hexahydro-1H-isoindole-1,3-dione hydrochloride crystals so obtained weighed 3.0 g, m.p.=242°-245° C.
Aufarbeitung
- temperaturewas heated
- temperatureat reflux for 16 hours
- concentrationThe dark brown solution was concentrated to dryness on a rotary evaporator
- customThe crude residue was purified twice by flash chromatography over a silica gel column
- customThe pure product thus obtained
Quellen und Nachweise
- ORD-Eintrag
- ord-d0fc7407d3094e1ea2a8f768e88775a5
- Quelldatensatz
- uspto-grants-1997_04
- Patentnummer
- US05624927
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