Methyl iodide → HCID 21502460, compound

HRID 1288520Notes

Reaction equation

HRID 1288520 reaction equation
[CH3:1][CH:2]([N:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)/[CH:3]=[CH:4]/[CH:5]1[C:10]([CH3:12])([CH3:11])[CH2:9][CH2:8][CH:7]=[C:6]1[CH3:13].[CH3:20][I:21]>CO>[I-:21].[CH3:20][N+:14]1([CH:2]([CH3:1])/[CH:3]=[CH:4]/[CH:5]2[C:10]([CH3:12])([CH3:11])[CH2:9][CH2:8][CH:7]=[C:6]2[CH3:13])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 21502519HCID 21502519, compound

Product 1

HCID 21502460HCID 21502460, compoundYield 28.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-[1-methyl-3-(2,6,6-trimethyl-2-cyclohexenyl)-2(trans)-propenyl]piperidine (3.0 g) in a small amount of absolute methanol was added methyliodide (2.1 g) under cooling, and the reaction mixture was allowed to stand over night. The solvent of the reaction mixture was distilled off under reduced pressure, and the residue was dissolved in dil. hydrochloric acid. The aqueous solution was washed with ether, and then adjusted to an alkalinity by adding sodium bicarbonate. The aqueous solution was extracted with chloroform, and the chloroform layer was washed with water. After drying the chloroform layer, the solvent was distilled off under reduced pressure. The residue was dissolved in methanol and thereto was added ether, and then the mixture was allowed to stand under cooling. Precipitated crystals were gathered by filtration and recrystallized from a mixed solvent of methanol and ether to give crystals (1.3 g) of 1-methyl-1-[1-methyl-3-(2,6,6-trimethyl-2-cyclohexenyl)-2(trans)-propenyl]piperidinium iodide, m.p. 156°-158° C.

Workup

  1. temperatureunder cooling
  2. waitto stand over night
  3. distillationThe solvent of the reaction mixture was distilled off under reduced pressure
  4. dissolutionthe residue was dissolved in dil. hydrochloric acid
  5. washThe aqueous solution was washed with ether
  6. additionby adding sodium bicarbonate
  7. extractionThe aqueous solution was extracted with chloroform
  8. washthe chloroform layer was washed with water
  9. dry with materialAfter drying the chloroform layer
  10. distillationthe solvent was distilled off under reduced pressure
  11. dissolutionThe residue was dissolved in methanol
  12. additionwas added ether
  13. temperatureunder cooling
  14. customPrecipitated crystals
  15. filtrationwere gathered by filtration
  16. customrecrystallized from a mixed solvent of methanol and ether

Sources & evidence

ORD record
ord-b769c4820aca4f86887db845c9b16c13
Source dataset
uspto-grants-1976_10
Patent number
US03988373

Reaction notes

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