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

HRID 991493Notes

Reaction equation

HRID 991493 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-tetrahydoisoquinoline (G. E. Stokker, Tetrahedron Letters 1996, 37, 5453) (43.4g, 0.14 mol), potassium carbonate (104.3g, 0.75 mol), methanol (1 L) and water (150ml) 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-dbd54edc0e984c06873e7377f3db7e39
Source dataset
uspto-grants-2002_10
Patent number
US06465485B1

Reaction notes

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