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Piperazine → 1,6-Dimethyl-2-oxo-4-piperazin-1-yl-1,2-dihydro-quinoline-3-carbonitrile

HRID 970490
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 970490
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH3:12])[CH:10]=2)[N:5]([CH3:13])[C:4](=[O:14])[C:3]=1[C:15]#[N:16].[NH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1>ClCCl>[CH3:13][N:5]1[C:6]2[C:11](=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=2)[C:2]([N:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)=[C:3]([C:15]#[N:16])[C:4]1=[O:14]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 4837PiperazineHCID 210819594-Chloro-1,6-dimethyl-2-oxo-1,2-dihydro-quinoline-3-carbonitrile

Produkt 1

HCID 210819011,6-Dimethyl-2-oxo-4-piperazin-1-yl-1,2-dihydro-quinoline-3-carbonitrileAusbeute 88,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of Compound 23 (1 g, 4.3 mmol) in dichloromethane was added slowly to a stirred solution of piperazine (1.1 g, 12.9 mmol) in dichloromethane at room temperature. The solution was stirred overnight at room temperature. The solvent was removed under reduced pressure. The residue was taken in water, sonicated briefly, and filtered. The solids were dissolved in ethyl acetate and washed by water. The organic layer was dried over Na2SO4 and concentrated to yield 1.07 g (88%) yellow solids. M.P. 274° C. 1H NMR (DMSO-d6): δ 2.39 (s, 3H), 2.94 (m, 4H), 3.48 (m, 4H), 3.54 (s, 3H), 7.45 (d, J=8.6 Hz, 1H), 7.56 (dd, J=1.3, 8.6 Hz, 1H), 7.64 (s, 1H). EIMS m/z 283 (M+1).

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. customsonicated briefly
  3. filtrationfiltered
  4. dissolutionThe solids were dissolved in ethyl acetate
  5. washwashed by water
  6. dry with materialThe organic layer was dried over Na2SO4
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-57d73ba362d442d7b38e02e08304f467
Quelldatensatz
uspto-grants-2007_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07312220B2

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