Methyl iodide → HCID 86643173, compound

HRID 1808319Notes

Reaction equation

HRID 1808319 reaction equation
[C:1](O)(=O)C(O)=O.[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH2:17][C@:18]2([CH2:32][CH2:33][C:34]([NH2:36])=[O:35])[C:27]3[C:22](=[CH:23][C:24]([O:30][CH3:31])=[C:25]([O:28][CH3:29])[CH:26]=3)[CH2:21][CH2:20][NH:19]2)[CH:12]=[CH:13][C:14]=1[O:15][CH3:16].[OH-].[Na+].ClCCl.[I:42]C>O>[I-:42].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH2:17][C@:18]2([CH2:32][CH2:33][C:34]([NH2:36])=[O:35])[C:27]3[C:22](=[CH:23][C:24]([O:30][CH3:31])=[C:25]([O:28][CH3:29])[CH:26]=3)[CH2:21][CH2:20][NH+:19]2[CH3:1])[CH:12]=[CH:13][C:14]=1[O:15][CH3:16]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 67537904HCID 67537904, compound

Product 1

HCID 86643173HCID 86643173, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(1R)-1-[(3,4-dimethoxyphenyl)methyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-2-aminocarbonylethylisoquinoline oxalate (7.0 g, 0.0139 moles) was dissolved in water (30 ml) and 20% aqueous sodium hydroxide solution was added to produce a pH in the range of 9-10. Dichloromethane (100 ml) was added and the mixture was stirred for 15 minutes at ambient temperature. The upper organic layer was separated and washed with 10% sodium chloride solution. The organic layer was dried over magnesium sulfate and evaporated under reduced pressure to afford an oily residue. Iodomethane (20 ml, 0.321 moles) was added to the oily residue. The mixture was stirred to obtain a solution and kept at ambient temperature overnight. The resulting precipitate was collected by filtration, washed with diethyl ether and dried to afford a mixture of 72% of the cis and 28% of the trans isomers of (1R)-1-[(3,4-dimethoxyphenyl)methyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-2-aminocarbonylethyl-isoquinolinium iodide (7.7 g; 99% yield).

Workup

  1. customto produce a pH in the range of 9-10
  2. customThe upper organic layer was separated
  3. washwashed with 10% sodium chloride solution
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. customevaporated under reduced pressure
  6. customto afford an oily residue
  7. stirringThe mixture was stirred
  8. customto obtain a solution
  9. waitkept at ambient temperature overnight
  10. filtrationThe resulting precipitate was collected by filtration
  11. washwashed with diethyl ether
  12. customdried
  13. customto afford

Sources & evidence

ORD record
ord-a90745def57d4d5e90f494bf45bb7cb1
Source dataset
uspto-grants-2013_01
Patent number
US08357807B2

Reaction notes

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