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Hydrogen Bromide → 1-[1-(4-Chlorophenyl)cyclobutyl]-2-ethyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrobromide

HRID 440489
Notes
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Reaction equation

HRID 440489 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH:12]3[C:21]4[C:16](=[CH:17][C:18]([O:24]C)=[C:19]([O:22]C)[CH:20]=4)[CH2:15][CH2:14][NH:13]3)[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH2:26](I)[CH3:27].C(=O)([O-])[O-].[K+].[K+].[BrH:35]>C(O)(=O)C.C(N(CC)CC)C.CC(C)=O>[BrH:35].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([CH:12]3[C:21]4[C:16](=[CH:17][C:18]([OH:24])=[C:19]([OH:22])[CH:20]=4)[CH2:15][CH2:14][N:13]3[CH2:26][CH3:27])[CH2:9][CH2:10][CH2:11]2)=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 260Hydrogen BromideHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 224067941-[1-(4-Chlorophenyl)cyclobutyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 224067431-[1-(4-Chlorophenyl)cyclobutyl]-2-ethyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrobromide

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolvent
HCID 180AcetoneSolvent
HCID 8471TriethylamineSolvent

Procedure

A mixture of 1-[1-(4-chlorophenyl)cyclobutyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (7.29 g prepared as described in Example 50), ethyl iodide (1.76 ml), anhydrous potassium carbonate (5.52 g) and acetone (100 ml) was heated under reflux for 16 hours. The reaction mixture was filtered and the solvent was removed by evaporation to give a residue which was digested with a 9:1 mixture of petroleum ether and triethylamine. The solution was filtered and the solvent removed to give a residue. A sample of this residue (4 g) was heated under reflux in a nitrogen atmosphere with glacial acetic acid (40 ml) and 48% hydrobromic acid (40 ml) for 20 hours. Removal of the solvent gave a residue which was dried by azeotropic distillation with industrial methylated spirit, then with propan-2-ol and finally with a mixture of toluene and propan-2-ol to give a solid which was washed with propan-2-ol and dried in vacuo at 80° C. to give 1-[1-(4-chlorophenyl)cyclobutyl]-2-ethyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrobromide, m.p. 213°-215° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 16 hours
  3. filtrationThe reaction mixture was filtered
  4. customthe solvent was removed by evaporation
  5. customto give a residue which
  6. filtrationThe solution was filtered
  7. customthe solvent removed
  8. customto give a residue
  9. customRemoval of the solvent
  10. customgave a residue which
  11. dry with materialwas dried by azeotropic distillation with industrial methylated spirit
  12. additionwith propan-2-ol and finally with a mixture of toluene and propan-2-ol
  13. customto give a solid which
  14. washwas washed with propan-2-ol
  15. customdried in vacuo at 80° C.

Sources & evidence

ORD record
ord-bd0e793d69b3407b82a85093061a52cc
Source dataset
uspto-grants-1996_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05519034

Reaction notes

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