5-(2-((2-(2-Ethoxyphenoxy)ethyl)amino)propyl)-2-methoxybenzenesulfonamide → Hydrochloric Acid

HRID 275113Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 275113
[CH2:1]([O:3][C:4]1[CH:28]=[CH:27][CH:26]=[CH:25][C:5]=1[O:6][CH2:7][CH2:8][NH:9][CH:10]([CH3:24])[CH2:11][C:12]1[CH:13]=[CH:14][C:15]([O:22][CH3:23])=[C:16]([S:18]([NH2:21])(=[O:20])=[O:19])[CH:17]=1)[CH3:2].C(OC1C=CC=CC=1OCCBr)C.[ClH:42].C(O)C>C(O)C>[ClH:42].[CH2:1]([O:3][C:4]1[CH:28]=[CH:27][CH:26]=[CH:25][C:5]=1[O:6][CH2:7][CH2:8][NH:9][CH:10]([CH3:24])[CH2:11][C:12]1[CH:13]=[CH:14][C:15]([O:22][CH3:23])=[C:16]([S:18]([NH2:21])(=[O:19])=[O:20])[CH:17]=1)[CH3:2]

Komponenten

6

Edukt 3

HCID 1218295-(2-((2-(2-Ethoxyphenoxy)ethyl)amino)propyl)-2-methoxybenzenesulfonamideHCID 70101831-(2-Bromoethoxy)-2-ethoxybenzeneHCID 21887872Ethanol hydrochloride

Produkt 2

HCID 313Hydrochloric AcidHCID 1218295-(2-((2-(2-Ethoxyphenoxy)ethyl)amino)propyl)-2-methoxybenzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

In 120 ml of ethanol were dissolved 2.4 g of (R) (-)5[(2-amino-2-methyl)ethyl]-2-methoxybenzenesulfonamide and 1.2 g of 2-(o-ethoxyphenoxy)ethyl bromide, and the mixture was refluxed for 16 hours under heating. The solvent was distilled away, and after alkalifing the residue by the addition of 10% sodium hydroxide, and the oily material precipitated was extracted with ethyl acetate. The extract solution was washed with a saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate. The solvent was distilled away, and the residue was subjected to silica-gel column chromatography. The product was eluted with CHCl3 -methanol (9:5) to provide 1.5 g of the crude crystals of (R) (-)-5-[2-[[2-(o-ethoxyphenoxy)ethyl]amino]-2-methylethyl]-2-methoxybenzenesulfonamide, which was treated with HCl-ethanol to give a hydrochloric acid salt of (R) (-)-5-[2-[[2-(o-ethoxyphenoxy)ethyl]amino]-2-methylethyl]-2-methoxybenzenesulfonamide.

Aufarbeitung

  1. temperaturethe mixture was refluxed for 16 hours
  2. temperatureunder heating
  3. distillationThe solvent was distilled away
  4. additionby the addition of 10% sodium hydroxide
  5. customthe oily material precipitated
  6. extractionwas extracted with ethyl acetate
  7. washThe extract solution was washed with a saturated aqueous sodium chloride
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationThe solvent was distilled away
  10. washThe product was eluted with CHCl3 -methanol (9:5)
  11. customto provide 1.5 g of the crude crystals of (R) (-)-5-[2-[[2-(o-ethoxyphenoxy)ethyl]amino]-2-methylethyl]-2-methoxybenzenesulfonamide, which

Quellen und Nachweise

ORD-Eintrag
ord-24626da66d414e5690a165dbcbc61d79
Quelldatensatz
uspto-grants-1995_02
Patentnummer
US05391825

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