N,N'-Dimethylethylenediamine → HCID 71252179, Verbindung

HRID 2411387Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2411387
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]1[CH2:14][CH2:13][N:12]([C:15]([C:17]2[CH:22]=[CH:21][C:20](I)=[CH:19][CH:18]=2)=[O:16])[CH2:11][CH2:10]1.[CH2:24]([C@@H:26]1[CH2:30][CH2:29][S:28](=[O:32])(=[O:31])[NH:27]1)[CH3:25].C(=O)([O-])[O-].[K+].[K+].CNCCNC>[Cu]I.O.C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]1[CH2:14][CH2:13][N:12]([C:15]([C:17]2[CH:22]=[CH:21][C:20]([N:27]3[C@H:26]([CH2:24][CH3:25])[CH2:30][CH2:29][S:28]3(=[O:32])=[O:31])=[CH:19][CH:18]=2)=[O:16])[CH2:11][CH2:10]1

Komponenten

8

Edukt 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 58484733[4-(2,4-Dimethylphenyl)piperazin-1-yl](4-iodophenyl)methanoneHCID 86676750HCID 86676750, Verbindung

Produkt 1

HCID 71252179HCID 71252179, VerbindungAusbeute 31,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a mixture of [4-(2,4-dimethylphenyl)piperazin-1-yl](4-iodophenyl)methanone (420 mg) described in Preparation Example 108, (R)-3-ethylisothiazolidine 1,1-dioxide (150 mg) described in Preparation Example 3, potassium carbonate (276 mg) and copper(I) iodide (95 mg) were added toluene (3 mL) and N,N′-dimethylethylenediamine (110 μL), and the mixture was stirred with heating under reflux for 8 hr. The reaction mixture was cooled, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and the solvent was evaporated. The obtained residue was purified by column chromatography (hexane:ethyl acetate) to give the title compound (140 mg).

Aufarbeitung

  1. temperaturewith heating
  2. temperatureunder reflux for 8 hr
  3. temperatureThe reaction mixture was cooled
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. customthe solvent was evaporated
  7. customThe obtained residue was purified by column chromatography (hexane:ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-447deea60954486fafc77f3be7f32db5
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08816079B2

Notizen zur Reaktion

Wird geladen…