Potassium Iodide → HCID 21500250, compound

HRID 1729806Notes

Reaction equation

HRID 1729806 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH3:11])=[O:9])[CH:4]([CH3:12])[CH2:3]1.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>>[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])[CH:4]([CH3:12])[CH2:3]2)=[C:15]([N+:21]([O-:23])=[O:22])[CH:16]=1

Participants

6

Reactant 5

HCID 4875Potassium IodideHCID 69772,5-DichloronitrobenzeneHCID 7966CyclohexanolHCID 10340Sodium CarbonateHCID 21500269HCID 21500269, compound

Product 1

HCID 21500250HCID 21500250, compound

Conditions

Temperature
160 °C

Procedure

A mixture of 44 parts of methyl 4-amino-2-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 for 10 hours at 160° C. After cooling, the reaction mixture is evaporated and water is added to the residue. The product is extracted with methylbenzene. The extract is washed successively twice with water and twice with a diluted hydrochloric acid solution. The formed precipitate is filtered off over hyflo. The filtrate is washed twice with water, dried, filtered and evaporated. The residue is stirred in 2,2'-oxybispropane with activated charcoal. The latter is filtered off and the clear filtrate is evaporated. The oily residue is purified by column-chromatography over silicagel, using trichloromethane as eluent. The pure fractions are collected and the eluent is evaporated, yielding methyl 4-(4-chloro-2-nitrophenylamino)-2-methyl-1-piperidinecarboxylate as an oily residue.

Workup

  1. temperatureAfter cooling
  2. customthe reaction mixture is evaporated
  3. additionwater is added to the residue
  4. extractionThe product is extracted with methylbenzene
  5. washThe extract is washed successively twice with water and twice with a diluted hydrochloric acid solution
  6. filtrationThe formed precipitate is filtered off over hyflo
  7. washThe filtrate is washed twice with water
  8. customdried
  9. filtrationfiltered
  10. customevaporated
  11. stirringThe residue is stirred in 2,2'-oxybispropane with activated charcoal
  12. filtrationThe latter is filtered off
  13. customthe clear filtrate is evaporated
  14. customThe oily residue is purified by column-chromatography over silicagel
  15. customThe pure fractions are collected
  16. customthe eluent is evaporated

Sources & evidence

ORD record
ord-26737aab0be04a3b8c989ffb6aa06a48
Source dataset
uspto-grants-1976_11
Patent number
US03989707

Reaction notes

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