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Dimethylformamide → 4-{1-Methyl-1-[4-(toluene-4-sulfonyl)-piperazin-1-yl]-ethyl]-benzonitrile

HRID 717076
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 717076
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:11]2[CH2:16][CH2:15][N:14]([S:17]([C:20]3[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=3)(=[O:19])=[O:18])[CH2:13][CH2:12]2)([CH3:10])[CH3:9])=[CH:4][CH:3]=1.[CH3:27][N:28](C=O)C>[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:9][C:8]([C:5]1[CH:6]=[CH:7][C:2]([C:27]#[N:28])=[CH:3][CH:4]=1)([N:11]1[CH2:16][CH2:15][N:14]([S:17]([C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=2)(=[O:19])=[O:18])[CH2:13][CH2:12]1)[CH3:10]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 6228DimethylformamideHCID 898128531-[1-(4-Bromo-phenyl)-1-methyl-ethyl]-4-(toluene-4-sulfonyl)-piperazine

Produkt 1

HCID 898128254-{1-Methyl-1-[4-(toluene-4-sulfonyl)-piperazin-1-yl]-ethyl]-benzonitrileAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11186Zinc cyanide (Zn(CN)2)Katalysator
HCID 178418397
HCID 178418397, Verbindung
Katalysator

Versuchsvorschrift

To a solution of 1-[1-(4-bromo-phenyl)-1-methyl-ethyl]-4-(toluene-4-sulfonyl)-piperazine (200 mg, 0.45 mmol) in DMF (3 mL) was added zinc cyanide (64.41 mg, 0.54 mmol) and tetrakis(triphenylphosphine)palladium(0) (52 mg, 0.045 mmol) and the reaction mixture degassed for 10 min under N2. The reaction mixture was then subjected to microwave irradiation for 30 min at 180° C., afterwhich time the reaction was diluted with 1:1 CH2Cl2/EtOAc (20 mL), washed with water (2×10 mL), passed through a phase separation cartridge and concentrated in vacuo. The crude residue was purified by reverse phase preparative HPLC-MS to afford 4-{1-methyl-1-[4-(toluene-4-sulfonyl)-piperazin-1-yl]-ethyl]-benzonitrile as a cream solid (70 mg, 47%).

Aufarbeitung

  1. customthe reaction mixture degassed for 10 min under N2
  2. customirradiation for 30 min at 180° C.
  3. additionafterwhich time the reaction was diluted with 1:1 CH2Cl2/EtOAc (20 mL)
  4. washwashed with water (2×10 mL)
  5. custompassed through a phase separation cartridge
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was purified by reverse phase preparative HPLC-MS

Quellen und Nachweise

ORD-Eintrag
ord-22488617e9db48ec96da092b6bfaf5bc
Quelldatensatz
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09193689B2

Notizen zur Reaktion

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