Hydrochloric Acid → N-[1-(3,5-dibromo-4-methoxy-benzyl)-6-hydroxy-1,2,3,4-tetrahydro-isoquinolin-7-yl]-benzenesulfonamide hydrochloride

HRID 1358463Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1358463
C(O)(=O)C(O)=O.C([O:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][C:24]=1[NH:25][S:26]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)(=[O:28])=[O:27])[CH:21]([CH2:35][C:36]1[CH:41]=[C:40]([Br:42])[C:39]([O:43][CH3:44])=[C:38]([Br:45])[CH:37]=1)[NH:20][CH2:19][CH2:18]2)C1C=CC=CC=1.[OH-].[Na+].C(Cl)[Cl:49].Cl>CO>[ClH:49].[Br:45][C:38]1[CH:37]=[C:36]([CH:41]=[C:40]([Br:42])[C:39]=1[O:43][CH3:44])[CH2:35][CH:21]1[C:22]2[C:17](=[CH:16][C:15]([OH:14])=[C:24]([NH:25][S:26]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)(=[O:28])=[O:27])[CH:23]=2)[CH2:18][CH2:19][NH:20]1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 18184536N-[6-benzyloxy-1-(3,5-dibromo-4-methoxy-benzyl)-1,2,3,4-tetrahydro-isoquinolin-7-yl]-benzenesulfonamide oxalateHCID 23721229Sodium hydroxide methylene chloride

Produkt 1

HCID 18184514N-[1-(3,5-dibromo-4-methoxy-benzyl)-6-hydroxy-1,2,3,4-tetrahydro-isoquinolin-7-yl]-benzenesulfonamide hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

N-[6-benzyloxy-1-(3,5-dibromo-4-methoxy-benzyl)-1,2,3,4-tetrahydro-isoquinolin-7-yl]-benzenesulfonamide oxalate (0.389 g, 0.00051 mol) was neutralized in a mixture 1N NaOH-methylene chloride. A free base was dissolved in a methanol—conc. HCl mixture (35 mL of each). The reaction mixture was refluxed for 1h and evaporated. HCl salt was neutralized with conc. NaHCO3 solution. The product was purified by column chromatography (silica gel, chloroform-methanol—aq. ammonia/100:10:1) and dissolved in methanol, a solution of fumaric acid in methanol was added. A fumaric salt was crystallized from methanol—ethyl ether mixture.

Aufarbeitung

  1. customevaporated
  2. customThe product was purified by column chromatography (silica gel, chloroform-methanol—aq. ammonia/100:10:1)
  3. dissolutiondissolved in methanol
  4. additiona solution of fumaric acid in methanol was added
  5. customA fumaric salt was crystallized from methanol—ethyl ether mixture

Quellen und Nachweise

ORD-Eintrag
ord-ed68bad863ff45f3b958920af3aff80a
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06596734B1

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