Potassium Hydroxide → 5-Bromo-3,3-dimethyl-1,2,3,4-tetrahydroisoquinoline

HRID 716640Notes

Reaction equation

HRID 716640 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][C:5]([CH3:17])([CH3:16])[N:6](C(OC)=O)[CH2:7]2.[OH-].[K+]>C(O)CO.O>[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][C:5]([CH3:17])([CH3:16])[NH:6][CH2:7]2

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 89500998HCID 89500998, compound

Product 1

HCID 846296205-Bromo-3,3-dimethyl-1,2,3,4-tetrahydroisoquinolineYield 40.5%

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of Intermediate 24E (4.6 g) in ethylene glycol (50 mL) was added 50% aqueous KOH solution (23 mL) and the reaction was heated at 150° C. for 3 days. The reaction mixture was cooled, diluted with H2O, extracted with EtOAc twice. The combined organics were extracted with 1.5 N HCl solution, the aqueous layer was basified with 10% NaOH solution, extracted with EtOAc twice and the combined organics were washed with H2O, brine, dried over Na2SO4, filtered and concentrated to give Intermediate 24 (1.5 g, 39.4%) as a brown liquid. MS (ESI) m/z: 242.2 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with EtOAc twice
  3. extractionThe combined organics were extracted with 1.5 N HCl solution
  4. extractionextracted with EtOAc twice
  5. washthe combined organics were washed with H2O, brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-01f7f50f506d4f88ab4124cd93c13b33
Source dataset
uspto-grants-2015_11
Patent number
US09192607B2

Reaction notes

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