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Potassium Carbonate → 8-Bromo-1,2,3,4-tetrahydroisoquinoline

HRID 1712944
Notes
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Reaction equation

HRID 1712944 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Br:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[CH2:14][N:13](C(=O)C(F)(F)F)[CH2:12][CH2:11]2.[Br:24][C:25]1[CH:26]=[CH:27][CH:28]=[C:29]2[C:34]=1[CH2:33][N:32](C(=O)C(F)(F)F)[CH2:31][CH2:30]2>CO.O.CCOC(C)=O>[Br:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[CH2:14][NH:13][CH2:12][CH2:11]2.[Br:24][C:25]1[CH:26]=[CH:27][CH:28]=[C:29]2[C:34]=1[CH2:33][NH:32][CH2:31][CH2:30]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 231554111-(6-bromo-3,4-dihydroisoquinolin-2(1H)-yl)-2,2,2-trifluoroethanoneHCID 594631661-(8-Bromo-3,4-dihydroisoquinolin-2(1H)-yl)-2,2,2-trifluoroethanone

Product 2

HCID 126304208-Bromo-1,2,3,4-tetrahydroisoquinolineYield 100%HCID 158851836-Bromo-1,2,3,4-tetrahydroisoquinoline

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Potassium carbonate (66.2 mmol) was added in one portion to a solution of 6-bromo-2-(trifluoroacetyl)-1,2,3,4-tetrahydroisoquinoline and 8-bromo-2-(trifluoroacetyl)-1,2,3,4-tetrahydroisoquinoline (17.6 mmol) in MeOH (130 mL) and water (45 mL). The reaction mixture was allowed to stir at rt overnight and then diluted with EtOAc (150 mL). The mixture was washed with brined, dried over Na2SO4, filtered, and concentrated to give 6-bromo-1,2,3,4-tetrahydroisoquinoline and 8-bromo-1,2,3,4-tetrahydroisoquinoline (5.0 g, 100%) as a white solid.

Workup

  1. washThe mixture was washed with brined,
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e06cd4c0c2364d21bf1ea8f8c4de3e62
Source dataset
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07795249B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes