Methanol → 7-Bromo-1,2,3,4-tetrahydroisoquinoline

HRID 1856787Notes

Reaction equation

HRID 1856787 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8](C(=O)C(F)(F)F)[CH2:9]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].CO.O>CCCCCC>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][NH:8][CH2:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 11430Potassium CarbonateHCID 109688311-(7-Bromo-3,4-dihydroisoquinolin-2(1H)-yl)-2,2,2-trifluoroethanone

Product 1

HCID 107292557-Bromo-1,2,3,4-tetrahydroisoquinolineYield 60%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A mixture of 7-bromo-2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinoline (G. E. Stokker, Tetrahedron Letters 1996, 37, 5453) (43.4 g, 0.14 mol), potassium carbonate (104.3 g, 0.75 mol), methanol (1 L) and water (150 ml) was heated at reflux for 1 h, then cooled and evaporated in vacuo. Residue was partitioned between water (1 L) and dichloromethane (4×200 ml). Combined extracts were dried (Na2SO4) and evaporated in vacuo to give an oil which was dissolved in hexane. The mixture was filtered and the filtrate evaporated in vacuo to give the title compound as an oil (17.7 g, 60%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 h
  3. temperaturecooled
  4. customevaporated in vacuo
  5. customResidue was partitioned between water (1 L) and dichloromethane (4×200 ml)
  6. dry with materialCombined extracts were dried (Na2SO4)
  7. customevaporated in vacuo
  8. customto give an oil which
  9. filtrationThe mixture was filtered
  10. customthe filtrate evaporated in vacuo

Sources & evidence

ORD record
ord-8dcd00871b224ef09e0bef50a7aadcee
Source dataset
uspto-grants-2000_11
Patent number
US06143762

Reaction notes

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