1-Methylpiperazine → 8-(4-Methyl-piperazin-1-yl)-3phenylsulfonylquinoline

HRID 883530Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 883530
I[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([S:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:14])=[O:13])=[CH:7]2.[CH3:21][N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1.CC(C)([O-])C.[Na+]>C1(P[C-]2C=CC=C2)C=CC=CC=1.[C-]1(PC2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH3:21][N:22]1[CH2:27][CH2:26][N:25]([C:2]2[CH:3]=[CH:4][CH:5]=[C:6]3[C:11]=2[N:10]=[CH:9][C:8]([S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=[O:14])=[O:13])=[CH:7]3)[CH2:24][CH2:23]1

Komponenten

5

Edukt 3

HCID 531671-MethylpiperazineHCID 114067748-Iodo-3-(phenylsulfonyl)quinolineHCID 23676156Sodium t-butoxide

Produkt 1

HCID 99291628-(4-Methyl-piperazin-1-yl)-3phenylsulfonylquinoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 133083342Bis(cyclopenta-2,4-dien-1-yl(phenyl)phosphane);iron(2+)Katalysator

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

8-Iodo-3-phenylsulfonyl-quinoline (D6) (190 mg, 0.48 mmol), N-methyl-piperazine (48 mg, 0.48 mmol), sodium tertbutoxide (65 mg, 0.68 mmol), di-palladium tetrakis-(dibenzylidine acetone) [Pd2(dba)3] (88 mg, 0.1 mmol) and 1,1′-diphenylphosphino ferrocene (161 mg, 0.3 mmol) were suspended in degassed dry dioxan (2 ml). The mixture was stirred under argon at 40° C. for 16 hours. The solvent was removed and the residue subjected to flash chromatography on silica gel (eluting with dichloromethane—methanol aq. ammonia) to give the title compound (E1), identical spectroscopically to that prepared by the earlier methods.

Aufarbeitung

  1. customin degassed dry dioxan (2 ml)
  2. customThe solvent was removed

Quellen und Nachweise

ORD-Eintrag
ord-a064bac4f8b442ec913444ae6f2e98e0
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08236947B2

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