N,N'-Dimethylethylenediamine → 1-[4-(1-Methoxy-1-methyl-ethyl)-phenyl]-3-(2-piperazin-1-yl-benzyl)-pyrrolidin-2-one

HRID 905610

Reaktionsgleichung

Reaktionsgleichung von HRID 905610
[N:1]1([C:7]2[CH:19]=[CH:18][CH:17]=[CH:16][C:8]=2[CH2:9][CH:10]2[CH2:14][CH2:13][NH:12][C:11]2=[O:15])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Br[C:21]1[CH:26]=[CH:25][C:24]([C:27]([O:30][CH3:31])([CH3:29])[CH3:28])=[CH:23][CH:22]=1.CNCCNC.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.[Cu]I>[CH3:31][O:30][C:27]([C:24]1[CH:25]=[CH:26][C:21]([N:12]2[CH2:13][CH2:14][CH:10]([CH2:9][C:8]3[CH:16]=[CH:17][CH:18]=[CH:19][C:7]=3[N:1]3[CH2:2][CH2:3][NH:4][CH2:5][CH2:6]3)[C:11]2=[O:15])=[CH:22][CH:23]=1)([CH3:29])[CH3:28]

Komponenten

7

Edukt 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 150723851-Bromo-4-(2-methoxypropan-2-yl)benzeneHCID 597825603-(2-Piperazin-1-yl-benzyl)-pyrrolidin-2-one

Produkt 1

HCID 597825671-[4-(1-Methoxy-1-methyl-ethyl)-phenyl]-3-(2-piperazin-1-yl-benzyl)-pyrrolidin-2-oneAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

3-(2-piperazin-1-yl-benzyl)-pyrrolidin-2-one (6) (1.2 grams) was subsequently allowed to react with 1.27 g of 1-bromo-4-(1-methoxy-1-methyl-ethyl)-benzene (11) in the presence of 0.041 grams of N,N′-dimethylethylenediamine, 0.088 g of CuI and 0.96 grams of K2CO3 in toluene (6 mL) at 110° C. for 17 hours to provide 1.2 grams of the racemate 1-[4-(1-methoxy-1-methyl-ethyl)-phenyl]-3-(2-piperazin-1-yl-benzyl)-pyrrolidin-2-one (12) (64% yield) following silica gel chromatography (40:1:0.5 chloroform-methanol-ammonium hydroxide); MS (AP/CI) observed: 408.2 (M+H)+.

Quellen und Nachweise

ORD-Eintrag
ord-1d27c8dd34804c87a1415110fcf4e794
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08012969B2

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