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

HRID 1358463Notes

Reaction equation

HRID 1358463 reaction equation
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

Participants

5

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-ed68bad863ff45f3b958920af3aff80a
Source dataset
uspto-grants-2003_07
Patent number
US06596734B1

Reaction notes

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