Hydrogen Bromide → HCID 22406867, compound

HRID 440472Notes

Reaction equation

HRID 440472 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1([CH:11]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([O:21]C)[CH:19]=3)[CH2:14][CH2:13][N:12]2[CH3:23])[CH2:10][CH2:9]1.[BrH:24]>C(O)(=O)C>[BrH:24].[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1([CH:11]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([OH:21])[CH:19]=3)[CH2:14][CH2:13][N:12]2[CH3:23])[CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 22406745HCID 22406745, compound

Product 1

HCID 22406867HCID 22406867, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1-[1-(2-Chlorophenyl)cyclopropyl]-7-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline (0.25 g, prepared as described in Example MF7) was heated on a steam bath at 100° C. in a solution of 48% hydrobromic acid (60 ml) and glacial acetic acid (60 ml) for 16 hours. The mixture was heated under reflux for 2 hours until the reaction was complete. The solvent was removed in vacuo and the residue dried by azeotropic distillation with propan-2-ol. The resulting suspension was removed by filtration and crystallised twice from ethanol to give 1-(1-(2-chlorophenyl)cyclopropyl)-7-hydroxy-2-methyl-1,2,3,4-tetrahydroisoquinoline hydrobromide, which was characterised by elemental analysis.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2 hours until the reaction
  3. customThe solvent was removed in vacuo
  4. dry with materialthe residue dried by azeotropic distillation with propan-2-ol
  5. customThe resulting suspension was removed by filtration
  6. customcrystallised twice from ethanol

Sources & evidence

ORD record
ord-0e8dac735f5d46f0b5f09bb366c77d44
Source dataset
uspto-grants-1996_05
Patent number
US05519034

Reaction notes

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