Water → 1-(4-Nitrophenyl)piperidin-4-one

HRID 1085264Notes

Reaction equation

HRID 1085264 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7](F)=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl.[NH:12]1[CH2:17][CH2:16][C:15](=[O:18])[CH2:14][CH2:13]1.C(N(CC)CC)C.O>C(#N)C>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:12]2[CH2:17][CH2:16][C:15](=[O:18])[CH2:14][CH2:13]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 9590p-FluoronitrobenzeneHCID 30848514-Piperidone hydrochloride

Product 1

HCID 38425621-(4-Nitrophenyl)piperidin-4-oneYield 79.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In 20 ml of acetonitrile were dissolved 2.8 g of 4-nitrofluorobenzene, 3 g of 4-piperidone hydrochloride and 6.9 ml of triethylamine, and the solution was then heated under reflux for 6 hours. After cooling, the reaction mixture was poured into 100 ml of water, and the deposited crystals were collected by filtration. The crystals were washed with water and then with ether, and they were recrystallized from isopropanol/hexane (1/1 in terms of volume ratio), collected by filtration, washed, and dried in order to obtain 3.47 g of 1-(4-nitrophenyl)-4-oxopiperidine (compound 62).

Workup

  1. temperaturethe solution was then heated
  2. temperatureunder reflux for 6 hours
  3. temperatureAfter cooling
  4. filtrationthe deposited crystals were collected by filtration
  5. washThe crystals were washed with water
  6. customwith ether, and they were recrystallized from isopropanol/hexane (1/1 in terms of volume ratio)
  7. filtrationcollected by filtration
  8. washwashed
  9. customdried in order

Sources & evidence

ORD record
ord-802e2a458e6040bfa26d4c2fada5112e
Source dataset
uspto-grants-1991_04
Patent number
US05008267

Reaction notes

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