Ethanol → 1-(4-Aminobenzoyl)-4-(4-fluorobenzoyl)piperidine

HRID 648508Notes

Reaction equation

HRID 648508 reaction equation
[F:1][C:2]1[CH:26]=[CH:25][C:5]([C:6]([CH:8]2[CH2:13][CH2:12][N:11]([C:14](=[O:24])[C:15]3[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=3)[CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1.[Cl-].[NH4+].O.C(O)C>[Fe].COCCO>[NH2:21][C:18]1[CH:17]=[CH:16][C:15]([C:14]([N:11]2[CH2:10][CH2:9][CH:8]([C:6](=[O:7])[C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:26][CH:25]=3)[CH2:13][CH2:12]2)=[O:24])=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 962WaterHCID 25517Ammonium ChlorideHCID 136039654-(4-Fluorobenzoyl)-1-(4-nitrobenzoyl)piperidine

Product 1

HCID 136039661-(4-Aminobenzoyl)-4-(4-fluorobenzoyl)piperidineYield 82.8%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 80192-MethoxyethanolSolvent

Procedure

4-(4-Fluorobenzoyl)-1-(4-nitrobenzoyl)piperidine (4.75 g) was added slowly to a stirred mixture of iron powder (4.75 g), ammonium chloride (0.57 g), water (28.5 ml), ethanol (38 ml) and methyl cellosolve (76 ml) under reflux. The resulting mixture was stirred under reflux for 30 minutes and filtered. The filtrate was concentrated in vacuo. The residue was diluted with saturated sodium bicarbonate solution and extracted twice with methylene chloride. The extract was washed with brine, dried over magnesium sulfate and concentrated in vacuo. The resulting residue was recrystallized from ethanol to give 1-(4-aminobenzoyl)-4-(4-fluorobenzoyl)piperidine (3.6 g) as pale yellow crystals.

Workup

  1. temperatureunder reflux
  2. temperatureunder reflux for 30 minutes
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. additionThe residue was diluted with saturated sodium bicarbonate solution
  6. extractionextracted twice with methylene chloride
  7. washThe extract was washed with brine
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated in vacuo
  10. customThe resulting residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-0dc91b587ee640f7a0e3c6f12d266405
Source dataset
uspto-grants-1988_04
Patent number
US04735952

Reaction notes

Loading…