Potassium Iodide → HCID 21500238, compound

HRID 1729798Notes

Reaction equation

HRID 1729798 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH3:11])=[O:9])[CH2:4][CH:3]1[CH3:12].Cl[C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=1[N+:21]([O-:23])=[O:22].C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+].C1(O)CCCCC1>O>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([NH:1][CH:2]2[CH2:7][CH2:6][N:5]([C:8]([O:10][CH3:11])=[O:9])[CH2:4][CH:3]2[CH3:12])=[C:15]([N+:21]([O-:23])=[O:22])[CH:16]=1

Participants

7

Reactant 5

HCID 4875Potassium IodideHCID 69772,5-DichloronitrobenzeneHCID 7966CyclohexanolHCID 10340Sodium CarbonateHCID 19785295Methyl 4-amino-3-methylpiperidine-1-carboxylate

Product 1

HCID 21500238HCID 21500238, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 43 parts of methyl 4-amino-3-methyl-1-piperidinecarboxylate, 57.6 parts of 1,4-dichloro-2-nitrobenzene, 32 parts of sodium carbonate, 0.2 parts of potassium iodide and 160 parts of cyclohexanol is stirred and refluxed (160°-163° C) for 20 hours with water-separator. The reaction mixture is evaporated. Water is added and the product is extracted with methylbenzene. The extract is dried, filtered and evaporated. The residue is purified by column-chromatography over silicagel, using a mixture of trichloromethane and 5% of methanol as eluent. The pure fractions are collected and the eluent is evaporated. Methylbenzene is added to the oily residue and the whole is washed with a diluted hydrochloric acid solution. After filtration over hyflo, the layers are separated. The methylbenzene phase is treated with activated charcoal. The latter is filtered off and the filtrate is dried, filtered and evaporated, yielding methyl 4-(4-chloro-2-nitrophenylamino)-3-methyl-1-piperidinecarboxylate as an oily residue.

Workup

  1. customThe reaction mixture is evaporated
  2. additionWater is added
  3. extractionthe product is extracted with methylbenzene
  4. customThe extract is dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is purified by column-chromatography over silicagel
  8. additiona mixture of trichloromethane and 5% of methanol as eluent
  9. customThe pure fractions are collected
  10. customthe eluent is evaporated
  11. additionMethylbenzene is added to the oily residue
  12. washthe whole is washed with a diluted hydrochloric acid solution
  13. filtrationAfter filtration over hyflo
  14. customthe layers are separated
  15. additionThe methylbenzene phase is treated with activated charcoal
  16. filtrationThe latter is filtered off
  17. customthe filtrate is dried
  18. filtrationfiltered
  19. customevaporated

Sources & evidence

ORD record
ord-6466bd354eb3471aa406a53712217406
Source dataset
uspto-grants-1976_11
Patent number
US03989707

Reaction notes

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