Potassium Iodide → HCID 20382371, compound

HRID 1973805Notes

Reaction equation

HRID 1973805 reaction equation
Br[CH2:2][CH:3]=[CH2:4].[CH3:5][O:6][C:7]1[CH:8]=[C:9]([NH:13][C:14]2([C:20]([O:22][CH3:23])=[O:21])[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[CH:10]=[CH:11][CH:12]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>CC(C)CC(=O)C>[CH3:5][O:6][C:7]1[CH:8]=[C:9]([NH:13][C:14]2([C:20]([O:22][CH3:23])=[O:21])[CH2:19][CH2:18][N:17]([CH2:4][CH:3]=[CH2:2])[CH2:16][CH2:15]2)[CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 7841Allyl bromideHCID 10340Sodium CarbonateHCID 122981734-Piperidinecarboxylic acid, 4-[(3-methoxyphenyl)amino]-, methyl ester

Product 1

HCID 20382371HCID 20382371, compound

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 2.66 parts of 3-bromo-1-propene, 6.1 parts of methyl 4-[N-(3-methoxyphenyl)amino]-4-piperidinecarboxylate, 3.2 parts of sodium carbonate, 0.1 parts of potassium iodide and 100 parts of 4-methyl-2-pentanone is stirred and refluxed for 10 hours. The reaction mixture is cooled overnight to room temperature and poured onto water. The layers are separated and the organic phase is washed with water, dried, filtered and evaporated. The oily residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and 6% of methanol as eluent. The pure fractions are collected and the eluent is evaporated, yielding methyl 4-[(3-methoxyphenyl)amino]-1-(2-propenyl)-4-piperidinecarboxylate as an oily residue.

Workup

  1. temperaturerefluxed for 10 hours
  2. temperatureThe reaction mixture is cooled overnight to room temperature
  3. additionpoured onto water
  4. customThe layers are separated
  5. washthe organic phase is washed with water
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. customThe oily residue is purified by column-chromatography over silica gel using
  10. additiona mixture of trichloromethane and 6% of methanol as eluent
  11. customThe pure fractions are collected
  12. customthe eluent is evaporated

Sources & evidence

ORD record
ord-8e8b24d597ae456f9edea62777f97d49
Source dataset
uspto-grants-1976_12
Patent number
US03998834

Reaction notes

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