Piperidine, 1-methyl-4-(4-nitrophenoxy)-4-phenyl- → Piperidine, 4-(p-aminophenoxy)-1-methyl-4-phenyl-

HRID 2285916Notes

Reaction equation

HRID 2285916 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5]([O:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.[H][H]>CO.[Pd]>[NH2:21][C:18]1[CH:19]=[CH:20][C:15]([O:14][C:5]2([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]2)=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 3060390Piperidine, 1-methyl-4-(4-nitrophenoxy)-4-phenyl-HCID 178418361HCID 178418361, compound

Product 1

HCID 3060392Piperidine, 4-(p-aminophenoxy)-1-methyl-4-phenyl-Yield 50.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 1-methyl-4-(4-nitrophenoxy)-4-phenylpiperidine (4.4 g, 14.1 mM) in methanol (250 ml) was hydrogenated at 1 atmosphere and ambient temperature over 5% palladium on charcoal (500 mg) until the theoretical uptake of hydrogen had occurred (about 2 hours). The catalyst was removed by filtration and the solvent evaporated under reduced pressure. Recrystallisation of the residue from IPA gave the title compound (2 g) m.p. 174°-5°.

Workup

  1. custom(about 2 hours)
  2. customThe catalyst was removed by filtration
  3. customthe solvent evaporated under reduced pressure
  4. customRecrystallisation of the residue from IPA

Sources & evidence

ORD record
ord-087ae6c0a6d144b4b3419ed8322470da
Source dataset
uspto-grants-1982_04
Patent number
US04325953

Reaction notes

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