Potassium Iodide → Ethyl 4-((4-chloro-2-nitrophenyl)amino)piperidine-1-carboxylate

HRID 2417792Notes

Reaction equation

HRID 2417792 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][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>O.C1(C)C=CC=CC=1>[C:8]([N:5]1[CH2:4][CH2:3][CH:2]([NH:1][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[N+:21]([O-:23])=[O:22])[CH2:7][CH2:6]1)([O:10][CH2:11][CH3:12])=[O:9]

Participants

8

Reactant 5

HCID 4875Potassium IodideHCID 69772,5-DichloronitrobenzeneHCID 7966CyclohexanolHCID 10340Sodium CarbonateHCID 100867Ethyl 4-amino-1-piperidinecarboxylate

Product 1

HCID 104608Ethyl 4-((4-chloro-2-nitrophenyl)amino)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 0.25 mole of ethyl 4-amino-1-piperidinecarboxylate, 0.3 mole of 1,4-dichloro-2-nitrobenzene, 0.3 mole of sodium carbonate, 0.2 g of potassium iodide and 160 ml of cyclohexanol was stirred at 150° C. for 40 hours. After the mixture had been cooled, toluene and water were added and the organic layer was separated off, washed three times with water, dried and evaporated. The oily residue was dissolved in hot diisopropyl ether and the solution was stirred under reflux with active charcoal, filtered and left to crystallize. Melting point: 116° C.

Workup

  1. temperatureAfter the mixture had been cooled
  2. customthe organic layer was separated off
  3. washwashed three times with water
  4. customdried
  5. customevaporated
  6. dissolutionThe oily residue was dissolved in hot diisopropyl ether
  7. stirringthe solution was stirred
  8. temperatureunder reflux with active charcoal
  9. filtrationfiltered
  10. waitleft
  11. customto crystallize

Sources & evidence

ORD record
ord-d3365c33bd754018a197ca286e125ff6
Source dataset
uspto-grants-1984_09
Patent number
US04470989

Reaction notes

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