Benzylamine → 3-(4-{[6-(Benzylamino)hexyl]oxy}butyl)benzenesulfonamide

HRID 749234

Reaktionsgleichung

Reaktionsgleichung von HRID 749234
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:14]=[C:15]([S:19]([NH2:22])(=[O:21])=[O:20])[CH:16]=[CH:17][CH:18]=1.[CH2:23]([NH2:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[OH-].[Na+]>C1(C)C=CC=CC=1>[CH2:23]([NH:30][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:14]=[C:15]([S:19]([NH2:22])(=[O:21])=[O:20])[CH:16]=[CH:17][CH:18]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Komponenten

5

Edukt 3

HCID 7504BenzylamineHCID 14798Sodium HydroxideHCID 21895438Benzenesulfonamide, 3-[4-[(6-bromohexyl)oxy]butyl]-

Produkt 1

HCID 693156893-(4-{[6-(Benzylamino)hexyl]oxy}butyl)benzenesulfonamideAusbeute 50,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

3-[4-(6-Bromo-hexyloxy)-butyl]benzenesulfonamide (1.0 g) in toluene (4 ml) was added dropwise to benzylamine (0.65 g) and the resulting mixture heated at 80° C. for 6 h. The mixture was then cooled and 20% aqueous sodium hydroxide solution (50 ml) was added. The resulting mixture was extracted with ethyl acetate and the combined organic layers evaporated to dryness in vacuo. The residual oil was then purified by chromatography (DCM-IMS-NH3(aq) 100:10:1) to give the title compound (0.54 g) LC RT=3.89 min.

Aufarbeitung

  1. temperatureThe mixture was then cooled
  2. extractionThe resulting mixture was extracted with ethyl acetate
  3. customthe combined organic layers evaporated to dryness in vacuo
  4. customThe residual oil was then purified by chromatography (DCM-IMS-NH3(aq) 100:10:1)

Quellen und Nachweise

ORD-Eintrag
ord-bd3f499aa4be4adf9a9b12a82dd0a673
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07402598B2

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