Potassium Iodide → 1-Benzhydryl-4-[2-(2-oxo-3,3-diphenylpyrrolidin-1-yl)ethyl]piperazin-2-one

HRID 1667137Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1667137
Br[CH2:2][CH2:3][N:4]1[CH2:8][CH2:7][C:6]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:5]1=[O:21].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[CH3:30][N:31]([CH3:34])[CH:32]=[O:33]>>[CH:30]([N:31]1[CH2:34][CH2:5][N:4]([CH2:2][CH2:3][N:4]2[CH2:8][CH2:7][C:6]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:5]2=[O:21])[CH2:3][C:32]1=[O:33])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:14]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Komponenten

5

Edukt 4

HCID 4875Potassium IodideHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 673587991-(2-Bromoethyl)-3,3-diphenylpyrrolidin-2-one

Produkt 1

HCID 673777001-Benzhydryl-4-[2-(2-oxo-3,3-diphenylpyrrolidin-1-yl)ethyl]piperazin-2-one

Versuchsvorschrift

To a solution of the product from the Example 28A (0.182 g, 0.6 mmol) in N,N-dimethylformamide (5 mL) was added 1-(2-bromoethyl)-3,3-diphenylpyrrolidin-2-one (Example 64B, 0.2 g, 0.6 mmol), potassium carbonate (0.25 g, 1.8 mmol), and a catalytic amount of potassium iodide. The reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated in vacuo, and partitioned in H2O/dichloromethane. The organic layer was separated, dried over MgSO4, and concentrated. The obtained residue was chromatographed eluting with 5% methanol/dichloromethane to yield the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 7.31 (m, 10H), 7.20 (m, 11H), 3.50 (t, J=6.10 Hz, 2H), 3.38 (t, J=6.44 Hz, 2H), 3.33 (m, 2H), 3.00 (m, 2H), 2.71 (m, 4H), 2.58 (t, J=6.27 Hz, 2H), MS (ESI+) m/z 530 (M+H)+.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompartitioned in H2O/dichloromethane
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe obtained residue was chromatographed
  7. washeluting with 5% methanol/dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-2d57d9f29cde4a509d74e2785374aeee
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08044069B2

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