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

HRID 2220100Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2220100
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 roomtemperature, 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. temperatureAfter cooling to roomtemperature
  2. customthe solvent was evaporated to dryness
  3. customThe crude material was purified by flash chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-f31c261c8b7c4637a7bbc4ec5e64b60b
Quelldatensatz
uspto-grants-2008_08
Patentnummer
US07417043B2

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