Piperazine → 1-(3-(Methylsulfonyl)phenyl)piperazine

HRID 1070728Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1070728
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:3]=1.[NH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:11][S:8]([C:4]1[CH:3]=[C:2]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[CH:7]=[CH:6][CH:5]=1)(=[O:10])=[O:9]

Komponenten

6

Edukt 3

HCID 4837PiperazineHCID 2757146Benzene, 1-bromo-3-(methylsulfonyl)-HCID 23676156Sodium t-butoxide

Produkt 1

HCID 129889541-(3-(Methylsulfonyl)phenyl)piperazine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 1-bromo-3-methanesulfonyl-benzene (0.8 g), piperazine (1 g), sodium tert-butoxide (0.5 g) BINAP (42 mg) and [Pd2(dba)3 (38 mg) in toluene (7 ml) was heated under argon at 80° C. for 24 h. After cooling to room temperature, the solvent was evaporated to dryness. The crude material was purified by flash chromatography on silica gel using EtOAc. Yield 0.48 g: MS m/z (rel. intensity, 70 eV) 240 (M+, 17), 199 (12), 198 (bp), 119 (9), 56 (7).

Aufarbeitung

  1. customthe solvent was evaporated to dryness
  2. customThe crude material was purified by flash chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-12fce80713fe436d83fad2907efde3e6
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06903120B2

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