Methyl iodide → HCID 10752374, compound

HRID 345859Notes

Reaction equation

HRID 345859 reaction equation
[CH3:1][C:2]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][NH:3]1.[H-].[Na+].[CH3:20]I>CN(C)C=O>[CH3:1][C:2]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][N:3]1[CH3:20]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 130853136226-78-3

Product 1

HCID 10752374HCID 10752374, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (+)-1-methyl-1-phenyl-1,2,3,4-tetrahydroisoquinoline (1.0 g) in N,N-dimethylformamide (10 ml) was added sodium hydride (0.19 g) in ice-bath with stirring. After stirring for 30 minutes at room temperature, to the mixture was added methyl iodide (0.31 ml). And after stirring for an hour at room temperature, the mixture was poured into ice-water and extracted with ethyl acetate. The organic layer was washed with water, sodium chloride aqueous solution, dried over magnesium sulfate and evaporated in vacuo to give (+)-1,2-dimethyl-1-phenyl-1,2,3,4-tetrahydroisoquinoline (0.6 g).

Workup

  1. stirringAfter stirring for 30 minutes at room temperature, to the mixture
  2. stirringAnd after stirring for an hour at room temperature
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water, sodium chloride aqueous solution
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-e71f606af1a64499bc7900b99c9c5d0b
Source dataset
uspto-grants-1991_10
Patent number
US05059608

Reaction notes

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