1-Phenylpiperazine → 2-[2-(4-Phenylpiperazin-1-yl)ethyl]isoindole-1,3-dione

HRID 1516781Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1516781
[C:1]1([N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:14][CH2:15][N:16]1[C:20](=[O:21])[C:19]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:18]2[C:17]1=[O:26].CCN(CC)CC.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[C:1]1([N:7]2[CH2:12][CH2:11][N:10]([CH2:14][CH2:15][N:16]3[C:20](=[O:21])[C:19]4=[CH:22][CH:23]=[CH:24][CH:25]=[C:18]4[C:17]3=[O:26])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

7

Edukt 4

HCID 70961-PhenylpiperazineHCID 8471TriethylamineHCID 113251H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)-HCID 11430Potassium Carbonate

Produkt 1

HCID 85979842-[2-(4-Phenylpiperazin-1-yl)ethyl]isoindole-1,3-dione

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of 1-phenylpiperazine 2 (2.59 g, 15.98 mmol) was reacted with N-(2-bromoethyl)phthalimide (8.12 g, 31.96 mmol), Et3N (2.0 mL) and K2CO3 (8.0 g) in DMF (40 mL) and stirred at 70° C. under N2 overnight. After the reaction mixture was cooled down, water (100 mL) was added. The mixture was extracted with diethyl ether. The organic phase was combined and dried over Na2SO4. The solvent was removed under vacuo to give the crude product, which was purified by flash chromatography (Hexane/EtOac=1/1) to furnish 3a, 3.81 g (71%) 1HNMR (CDCl3) 2.68-2.72 (m, 6H, N(CH2)2, CONCH2), 3.12-3.15 (t, J=4.8 Hz, 4H, N(CH2)2), 3.84-3.89 (t, J=6.3 Hz, 2H), 6.80-6.82 (t, J=8.1 Hz, 1H, Ar—H), 6.88-6.91 (d, J=8.1 Hz, 2H, Ar—H), 7.21-7.26 (t, J=8.1 Hz, 2H, Ar—H), 7.69-7.86 (m, 4H, Ar—H).

Aufarbeitung

  1. temperatureAfter the reaction mixture was cooled down
  2. extractionThe mixture was extracted with diethyl ether
  3. dry with materialdried over Na2SO4
  4. customThe solvent was removed under vacuo
  5. customto give the crude product, which
  6. customwas purified by flash chromatography (Hexane/EtOac=1/1)

Quellen und Nachweise

ORD-Eintrag
ord-212ab999091d470f8665a510ab941233
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08227604B2

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