Potassium Iodide → HCID 86734316, compound

HRID 1973841Notes

Reaction equation

HRID 1973841 reaction equation
Br[CH2:2][CH:3]=[CH2:4].[O:5]=[C:6]([N:9]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:10]1([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)[CH2:7][CH3:8].[C:27](=[O:30])([O-:29])[O-].[Na+].[Na+].[I-].[K+]>CC(C)CC(=O)C>[C:16]([OH:18])(=[O:17])[C:27]([OH:29])=[O:30].[O:5]=[C:6]([N:9]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:10]1([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:15][CH2:14][N:13]([CH2:4][CH:3]=[CH2:2])[CH2:12][CH2:11]1)[CH2:7][CH3:8]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 7841Allyl bromideHCID 10340Sodium CarbonateHCID 12298181HCID 12298181, compound

Product 1

HCID 86734316HCID 86734316, compound

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 2.06 parts of 3-bromo-1-propene, 4.6 parts of ethyl 4-[(1-oxopropyl)phenylamino]-4-piperidinecarboxylate, 2,4 parts of sodium carbonate, 0.1 parts of potassium iodide and 80 parts of 4-methyl-2-pentanone is stirred and refluxed for 5 hours. After cooling to room temperature, the reaction mixture is poured onto water. The organic phase is separated, washed with water, dried, filtered and evapoarated. The oily residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and 5% of methanol as eluent. The pure fractions are collected and the eluent is evaorated. The oily residue is converted into the ethanedioate salt in 2-propanol. The salt is filtered off and crystallized from 8 parts of 2-propanol. The product is filtered off and dried, yielding 3.8 parts of ethyl 4-[(1-oxopropyl)phenylamino]-1-(2-propenyl)-4-piperidinecarboxylate ethanedioate; mp. 152.9° C.

Workup

  1. temperaturerefluxed for 5 hours
  2. additionthe reaction mixture is poured onto water
  3. customThe organic phase is separated
  4. washwashed with water
  5. customdried
  6. filtrationfiltered
  7. customThe oily residue is purified by column-chromatography over silica gel using
  8. additiona mixture of trichloromethane and 5% of methanol as eluent
  9. customThe pure fractions are collected
  10. filtrationThe salt is filtered off
  11. customcrystallized from 8 parts of 2-propanol
  12. filtrationThe product is filtered off
  13. customdried

Sources & evidence

ORD record
ord-32eeffec3a694e798421c7c520dbf895
Source dataset
uspto-grants-1976_12
Patent number
US03998834

Reaction notes

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