Water → HCID 10014061, compound

HRID 1667318Notes

Reaction equation

HRID 1667318 reaction equation
Cl.[CH3:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:4]=1/[CH:10]=[CH:11]/[CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][NH:13]1.[C:18](=O)([O-])[O-].[K+].[K+].O>CN(C)C=O.CI.C(N(CC)CC)C>[CH3:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([CH3:2])[C:4]=1/[CH:10]=[CH:11]/[CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][N:13]1[CH3:18]

Participants

7

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 67443477HCID 67443477, compound

Product 1

HCID 10014061HCID 10014061, compoundYield 99.2%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6328Methyl iodideSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 520 mg of 2-[(E)-2-(2,6-dimethylphenyl)vinyl]piperidine monohydrochloride in 7 ml of dimethylformamide, 0.13 ml of methyl iodide, 0.58 ml of triethylamine and 572 mg of potassium carbonate were added, followed by stirring at ambient temperature for 12 hours. The reaction mixture was poured into water, followed by extraction with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride and then dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated and the resulting residue was purified by silica gel column chromatography (chloroform-methanol) to give 470 mg of 2-[(E)-2-(2,6-dimethylphenyl)vinyl]-1-methylpiperidine. The product was dissolved in 5 ml of ethanol, and 2.5 ml of 35% hydrogen chloride-ethanol was added to the solution, followed by stirring at ambient temperature for 1 hour. The reaction mixture was evaporated under reduced pressure and the residue was azeotropically distilled with 5 ml of toluene 3 times to give crystals. The collected crystals were recrystallized from ethanol-ethyl acetate to give 395 mg of 2-[(E)-2-(2,6-dimethylphenyl)vinyl]-1-methylpiperidine monohydrochloride.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated
  6. customthe resulting residue was purified by silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-68a3badb3c5449b393605417367fa9e6
Source dataset
uspto-grants-2011_10
Patent number
US08044206B2

Reaction notes

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