Potassium Iodide → 1-Benzyl-N-(2-nitrophenyl)piperidin-4-amine

HRID 437656Notes

Reaction equation

HRID 437656 reaction equation
[C:1]1([CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([NH2:14])[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[N+:22]([O-:24])=[O:23].C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+].C1(O)CCCCC1>O>[N+:22]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[NH:14][CH:11]1[CH2:12][CH2:13][N:8]([CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:9][CH2:10]1)([O-:24])=[O:23]

Participants

7

Reactant 5

HCID 4875Potassium IodideHCID 69451-Chloro-2-nitrobenzeneHCID 7966CyclohexanolHCID 10340Sodium CarbonateHCID 4158521-Benzyl-4-piperidylamine

Product 1

HCID 816751-Benzyl-N-(2-nitrophenyl)piperidin-4-amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-15 °C

Procedure

A mixture of 38 parts of 1-(phenylmethyl)-4-piperidinamine, 40 parts of 2-chloronitrobenzene, 32 parts of sodium carbonate, a few crystals of potassium iodide in 320 parts of cyclohexanol is stirred and refluxed for 22 hours. After cooling, 300 parts of water are added. The organic layer is separated, diluted with 160 parts of water are added. The organic layer is separated, diluted with 160 parts of benzene and the whole is washed three times with 150 parts of water; the organic layer is dried over magnesium sulfate, filtered and evaporated. The residue is dissolved in a mixture of 40 parts of 2,2'-oxybispropane and 160 parts of hexane. After cooling to -15° C, the precipitate is filtered off and the filtrate is set aside. The precipitate is recrystallized from 160 parts of 2,2'-oxybispropane and filtered off, yielding 18.5 parts of N-(2-nitrophenyl)-1-(phenylmethyl)-4-piperidinamine; mp. 93.4°-94.6° C.

Workup

  1. temperaturerefluxed for 22 hours
  2. temperatureAfter cooling
  3. customThe organic layer is separated
  4. additiondiluted with 160 parts of water
  5. additionare added
  6. customThe organic layer is separated
  7. additiondiluted with 160 parts of benzene
  8. washthe whole is washed three times with 150 parts of water
  9. dry with materialthe organic layer is dried over magnesium sulfate
  10. filtrationfiltered
  11. customevaporated
  12. dissolutionThe residue is dissolved in a mixture of 40 parts of 2,2'-oxybispropane and 160 parts of hexane
  13. filtrationthe precipitate is filtered off
  14. customThe precipitate is recrystallized from 160 parts of 2,2'-oxybispropane
  15. filtrationfiltered off

Sources & evidence

ORD record
ord-251825ac6f014df581821ee40aaf0480
Source dataset
uspto-grants-1977_06
Patent number
US04031226

Reaction notes

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