Hydrogen Bromide → HCID 22406878, compound

HRID 440511Notes

Reaction equation

HRID 440511 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1([CH:12]2[C:21]3[C:16](=[CH:17][C:18]([F:24])=[C:19]([O:22]C)[CH:20]=3)[CH2:15][CH2:14][N:13]2[CH3:25])[CH2:11][CH2:10]1.[BrH:26]>C(O)(=O)C>[BrH:26].[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1([CH:12]2[C:21]3[C:16](=[CH:17][C:18]([F:24])=[C:19]([OH:22])[CH:20]=3)[CH2:15][CH2:14][N:13]2[CH3:25])[CH2:10][CH2:11]1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 22406718HCID 22406718, compound

Product 1

HCID 22406878HCID 22406878, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 1 -[1-(2,4 -dichlorophenyl)cyclopropyl]-6-fluoro-7-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline (8.5 g), 48% aqueous hydrobromic acid (100 ml) and glacial acetic acid (100 ml) was heated under reflux for 2 hours. The solvents were removed in vacuo and the residue dried by azeotropic distillation with propan-2-ol. The resulting solid was recrystallised from propan-2-ol to yield 1-[1-(2,4-dichlorophenyl)cyclopropyl]-6-fluoro-7-hydroxy-2-methyl-1,2,3,4-tetrahydroisoquinoline hydrobromide (7.2 g), m.p. 235°-237° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. customThe solvents were removed in vacuo
  4. dry with materialthe residue dried by azeotropic distillation with propan-2-ol
  5. customThe resulting solid was recrystallised from propan-2-ol

Sources & evidence

ORD record
ord-3a5bb97c057c44c18440a0337bc191a5
Source dataset
uspto-grants-1996_05
Patent number
US05519034

Reaction notes

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