HCID 12237072, compound → 1,1,2-Trimethyl-1,2,3,4-tetrahydroisoquinoline

HRID 2297609Notes

Reaction equation

HRID 2297609 reaction equation
[CH3:1][Mg]Br.[I-].[CH3:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][CH2:8][N+:7]=1[CH3:16]>C1COCC1>[CH3:5][C:6]1([CH3:1])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][CH2:8][N:7]1[CH3:16]

Participants

4

Reactant 2

HCID 12237072HCID 12237072, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 183826711,1,2-Trimethyl-1,2,3,4-tetrahydroisoquinoline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl magnesium bromide (4.5 ml, 3M in Et2O) was added to a stirred suspension of 1,2-dimethyl-3,4-dihydroisoquinolinium iodide (1.3 g) in dry THF (20 ml) at −70° C. under argon. After 1 h, the mixture was allowed to warm slowly to room temperature and stirred overnight. The mixture was quenched by cautious addition of water and extracted with ethyl acetate. The extract was washed with water, brine, dried (MgSO4) and evaporated in vacuo to give the title compound as a pink oil (730 mg).

Workup

  1. customThe mixture was quenched by cautious addition of water
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water, brine
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-dd92d7f7618845179b92dd1ae277b7d0
Source dataset
uspto-grants-2002_12
Patent number
US06492378B1

Reaction notes

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