1-Phenylpiperazine → 3-{3-[3-(4-Phenyl-piperazin-1-yl)-propoxy]-phenyl}-thieno[2,3-d]isoxazole

HRID 8652

Reaktionsgleichung

Br[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([C:12]2[C:16]3[S:17][CH:18]=[CH:19][C:15]=3[O:14][N:13]=2)[CH:9]=[CH:10][CH:11]=1.ClCCCOC1C=C(C2C3SC=CC=3ON=2)C=CC=1.[C:39]1([N:45]2[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]2)[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.C(=O)([O-])[O-].[K+].[K+]>>[C:39]1([N:45]2[CH2:50][CH2:49][N:48]([CH2:2][CH2:3][CH2:4][O:5][C:6]3[CH:7]=[C:8]([C:12]4[C:16]5[S:17][CH:18]=[CH:19][C:15]=5[O:14][N:13]=4)[CH:9]=[CH:10][CH:11]=3)[CH2:47][CH2:46]2)[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Komponenten

Edukt 4

HCID 70961-Phenylpiperazine

HCID 11430Potassium Carbonate

HCID 219835563-[3-(3-Chloro-propoxy)-phenyl]-thieno[2,3-d]isoxazole

HCID 219835593-[3-(3-Bromo-propoxy)phenyl]-thieno[2,3-d]isoxazole

Produkt 1

HCID 98667823-{3-[3-(4-Phenyl-piperazin-1-yl)-propoxy]-phenyl}-thieno[2,3-d]isoxazoleAusbeute 94 %

Versuchsvorschrift

The title compound is prepared from a mixture of 3-[3-(3-bromo-propoxy)-phenyl]-thieno[2,3-d]isoxazole, 3-[3-(3-chloro-propoxy)-phenyl]-thieno[2,3-d]isoxazole, 1-phenylpiperazine and potassium carbonate essentially as described above in example 4 except that the column is eluted with a mixture of dichloromethane:methanol (98:2). Combine the appropriate fractions and concentrate to give the title compound (0.36 g, 94% Yield) as an oil. Combine the appropriate fractions and concentrate to give the title compound (0.50 g, 100% Yield) as a solid. Purity by LC/MS (APCI)=100% area, [M+H]+=420 m/e.

Aufarbeitung

washis eluted with a mixture of dichloromethane:methanol (98:2)
concentrationCombine the appropriate fractions and concentrate

Quellen und Nachweise

ORD-Eintrag: ord-8285a2268d0743a5afb92970bebc1927
Quelldatensatz: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07091199B1

Verknüpfte Notizen

Wird geladen…