Potassium Carbonate → 7-(Trifluoromethyl)-1,2,3,4-tetrahydroisoquinoline

HRID 969559Notes

Reaction equation

HRID 969559 reaction equation
FC(F)(F)C([N:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][C:9]([C:15]([F:18])([F:17])[F:16])=[CH:10][CH:11]=2)[CH2:6]1)=[O:4].[C:21](=O)([O-])[O-:22].[K+].[K+]>C(O)C.O>[NH4+:5].[OH-:4].[CH3:21][OH:22].[F:18][C:15]([F:16])([F:17])[C:9]1[CH:8]=[C:7]2[C:12]([CH2:13][CH2:14][NH:5][CH2:6]2)=[CH:11][CH:10]=1

Participants

6

Reactant 2

HCID 11430Potassium CarbonateHCID 181765382-Trifluoroacetyl-7-trifluoromethyl-1,2,3,4-tetrahydroisoquinoline

Product 2

HCID 103755517-(Trifluoromethyl)-1,2,3,4-tetrahydroisoquinolineYield 116%HCID 21894508Ammonium hydroxide methanolYield 1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

2-(Trifluoroacetyl)-7-(trifluoromethyl)-1,2,3,4-tetrahydroisoquinoline (4.1 g, 12 mmol) was dissolved in ethanol (16.0 mL). Potassium carbonate (4.0 g, 29 mmol) and water (4 mL) were added and the mixture was refluxed for 2 h. After cooling, the solution was diluted with water and extracted with dichloromethane four times. The combined extracts were dried (MgSO4), filtered, and concentrated. Purification by high pressure chromatography on silica gel eluting with a gradient of 100% A to 20% B (A=1% NH4OH/5% MeOH/EtOAc; B=1% NH4OH/MeOH) over 13 min provided the title compound (1.4 g, 59%). MS calculated for C10H10F3N: (M+H)+202; found 202.0.

Workup

  1. temperaturethe mixture was refluxed for 2 h
  2. temperatureAfter cooling
  3. extractionextracted with dichloromethane four times
  4. dry with materialThe combined extracts were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by high pressure chromatography on silica gel eluting with a gradient of 100% A to 20% B (A=1% NH4OH/5% MeOH/EtOAc

Sources & evidence

ORD record
ord-cd950cdefe9343e1b346113c358c1e8e
Source dataset
uspto-grants-2007_12
Patent number
US07307086B2

Reaction notes

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