HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → N-[1-(3,5-dibromo-4-methoxy-benzyl)-6-hydroxy-1,2,3,4-tetrahydro-isoquinolin-7-yl]-benzenesulfonamide hydrochloride
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | N-[6-benzyloxy-1-(3,5-dibromo-4-methoxy-benzyl)-1,2,3,4-tetrahydro-isoquinolin-7-yl]-benzenesulfonamide oxalate | HCID 18184536 | — |
| Reactant | Sodium hydroxide methylene chloride | HCID 23721229 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | N-[1-(3,5-dibromo-4-methoxy-benzyl)-6-hydroxy-1,2,3,4-tetrahydro-isoquinolin-7-yl]-benzenesulfonamide hydrochloride | HCID 18184514 | — |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06596734B1 |
| Source dataset | uspto-grants-2003_07 |
| ORD ID | ord-ed68bad863ff45f3b958920af3aff80a |
| Source note | uspto-grants-2003_07 |