Hydrogen Bromide → HCID 22406799, compound

HRID 440474Notes

Reaction equation

HRID 440474 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([O:12]C)=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([CH3:24])[CH:7]2[C:14]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:17][CH2:16][CH2:15]1.[BrH:25]>C(O)(=O)C>[BrH:25].[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([CH3:24])[CH:7]2[C:14]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:15][CH2:16][CH2:17]1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 22406885HCID 22406885, compound

Product 1

HCID 22406799HCID 22406799, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 5-chloro-8-methoxy-2-methyl-1-(1-phenylcyclobutyl)-1,2,3,4-tetrahydroisoquinoline (5.5 g) prepared as described in Example MI5), 48% aqueous hydrobromic acid (50 ml) and glacial acetic acid (50 ml) was heated under reflux in a nitrogen atmosphere for 24 hours. The solvents were removed by evaporation The residue was decolourised with charcoal in methanol. The mixture was filtered and the solvent removed from the filtrate. The residue was dried by azeotropic distillation with propan-2-ol, and decolourised with charcoal in methanol. The mixture was filtered and the solvent removed from the filtrate. The residue was dried by azeotropic distillation with propan-2-ol and treated with ether to give 5-chloro-8-hydroxy-2-methyl-1-(1-phenylcyclobutyl)-1,2,3,4-tetrahydroisoquinoline hydrobromide, m.p. 197°-200° C. (dec).

Workup

  1. customprepared
  2. temperaturewas heated
  3. temperatureunder reflux in a nitrogen atmosphere for 24 hours
  4. customThe solvents were removed by evaporation The residue
  5. filtrationThe mixture was filtered
  6. customthe solvent removed from the filtrate
  7. dry with materialThe residue was dried by azeotropic distillation with propan-2-ol
  8. filtrationThe mixture was filtered
  9. customthe solvent removed from the filtrate
  10. dry with materialThe residue was dried by azeotropic distillation with propan-2-ol
  11. additiontreated with ether

Sources & evidence

ORD record
ord-d1f98f1d8f3b410e9d5bc2d0a00e5ca9
Source dataset
uspto-grants-1996_05
Patent number
US05519034

Reaction notes

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