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

HRID 2241084Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2241084
[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-7b1f33b1d7254e30a3793a2c50dfdd58
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07723519B2

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