1,2-Dichloroethane → (4-benzylpiperazin-1-yl)(1-(4-fluorobenzyl)-1H-indol-2-yl)methanone

HRID 83606

Reaktionsgleichung

Reaktionsgleichung von HRID 83606
[F:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[C:8]2[C:16]([OH:18])=O)=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[CH2:44]([N:51]1[CH2:56][CH2:55][NH:54][CH2:53][CH2:52]1)[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>C(OCC)C.C(OCC)(=O)C.CN(C=O)C>[CH2:44]([N:51]1[CH2:56][CH2:55][N:54]([C:16]([C:8]2[N:7]([CH2:6][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:20][CH:19]=3)[C:15]3[C:10]([CH:9]=2)=[CH:11][CH:12]=[CH:13][CH:14]=3)=[O:18])[CH2:53][CH2:52]1)[C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1

Komponenten

8

Edukt 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 759941-BenzylpiperazineHCID 81531DiisopropylethylamineHCID 186270691-(4-fluorobenzyl)-1H-indole-2-carboxylic acid

Produkt 1

HCID 66571096(4-benzylpiperazin-1-yl)(1-(4-fluorobenzyl)-1H-indol-2-yl)methanoneAusbeute 71,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 21584169Diethylether ethylacetateLösungsmittel

Versuchsvorschrift

The following was added sequentially to anhydrous DMF: 1-(4-fluorobenzyl)-1H-indole-2-carboxylic acid (50 mg, 0.186 mmol), Hunig's Base (0.065 ml, 0.371 mmol), EDC (46.3 mg, 0.241 mmol), HOBT (37.0 mg, 0.241 mmol), and 1-benzylpiperazine (32.7 mg, 0.186 mmol). The solution was allowed to stir at room temperature for 22 h. At this time, a 1:1 solution of diethylether/ethyl acetate (5 mL) was added, and this was washed with aqueous 10% Na2CO3 (3×2 mL). The extract was then dried with anhydrous MgSO4, filtered, and the filtrate was concentrated in vacuo. The crude residue was purified by column chromatography (20 g silica, 80% EtOAC/Hexanes) to provide 57 mg of the title compound.

Aufarbeitung

  1. washthis was washed with aqueous 10% Na2CO3 (3×2 mL)
  2. dry with materialThe extract was then dried with anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe crude residue was purified by column chromatography (20 g silica, 80% EtOAC/Hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-f9409ce4bfe340538e78425c0eebca35
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846684B2

Verknüpfte Notizen

Wird geladen…