Sulfuric Acid → 4-(4-Bromophenyl)-6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinoline

HRID 1072507Notes

Reaction equation

HRID 1072507 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](O)[CH2:9][N:10]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=2[Cl:20])[CH3:11])=[CH:4][CH:3]=1.OS(O)(=O)=O.[OH-].[Na+]>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:18]3[C:13](=[C:14]([Cl:20])[CH:15]=[C:16]([Cl:19])[CH:17]=3)[CH2:12][N:10]([CH3:11])[CH2:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 223868482-((2,4-Dichlorobenzyl)(methyl)amino)-1-(4-bromophenyl)ethanol

Product 1

HCID 101772114-(4-Bromophenyl)-6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolineYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5.45 g (14.0 mmol) of 1-(4-bromo-phenyl)-2-[(2,4-dichloro-benzyl)-methyl-amino]-ethanol was introduced into 15 ml of dichloromethane and, at 0° C., 15 ml of conc. H2SO4 are added. After stirring at room temperature for 2 hours, the reaction mixture was poured onto ice and made alkaline with 6 N NaOH. Three extractions with dichloromethane were carried out. The combined organic phases were dried with MgSO4 and concentrated. For further purification, the residue was chromatographed on silica gel, resulting in 2.6 g of the title compound as a yellowish oil. 4-(4-Bromo-phenyl)-6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinoline, Hydrochloride;

Workup

  1. additionthe reaction mixture was poured onto ice
  2. extractionThree extractions with dichloromethane
  3. dry with materialThe combined organic phases were dried with MgSO4
  4. concentrationconcentrated
  5. customFor further purification
  6. customthe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-e8bff8e7970649649270640a359d5372
Source dataset
uspto-grants-2005_06
Patent number
US06911453B2

Reaction notes

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