Ammonium Chloride → HCID 22494666, compound

HRID 1816745Notes

Reaction equation

HRID 1816745 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][C:13]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=3)([O:16][CH3:17])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-])=O.[Cl-].[NH4+]>C(O)C.O.[Fe]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:15][CH2:14][C:13]([C:18]3[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=3)([O:16][CH3:17])[CH2:12][CH2:11]2)=[CH:8][CH:9]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 22494673HCID 22494673, compound

Product 1

HCID 22494666HCID 22494666, compoundYield 89.8%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 1-(4-nitrophenyl)-4-(4-chlorophenyl)-4-methoxypiperidine (8.9 g), iron powder (10.7 g) and ammonium chloride (1.07 g) in ethanol (445 ml) and water (44.5 ml) was stirred at reflux for 5.5 hours. The insoluble material was filtered off, and the filtrate was evaporated under reduced pressure. To the residue was added a mixture of ethyl acetate (150 ml), water (100 ml) and saturated sodium hydrogen carbonate (50 ml). The organic layer was separated, washed with brine, dried over magnesium sulfate. The magnesium sulfate was filtered off, and the filtrate was evaporated under reduced pressure. To the residue was added a mixture of diisopropyl ether (10 ml) and n-hexane (20 ml). The precipitate was collected by filtration, and dried under reduced pressure to give 1-(4-aminophenyl)-4-(4-chlorophenyl)-4-methoxypiperidine (7.3 g).

Workup

  1. temperatureat reflux for 5.5 hours
  2. filtrationThe insoluble material was filtered off
  3. customthe filtrate was evaporated under reduced pressure
  4. additionTo the residue was added
  5. additiona mixture of ethyl acetate (150 ml), water (100 ml) and saturated sodium hydrogen carbonate (50 ml)
  6. customThe organic layer was separated
  7. washwashed with brine
  8. dry with materialdried over magnesium sulfate
  9. filtrationThe magnesium sulfate was filtered off
  10. customthe filtrate was evaporated under reduced pressure
  11. additionTo the residue was added
  12. additiona mixture of diisopropyl ether (10 ml) and n-hexane (20 ml)
  13. filtrationThe precipitate was collected by filtration
  14. customdried under reduced pressure

Sources & evidence

ORD record
ord-a72c3f2e107a4e1abeaa0599b0fa33c6
Source dataset
uspto-grants-2005_04
Patent number
US06884868B1

Reaction notes

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