HCID 20536592, compound → HCID 20542610, compound

HRID 2285910Notes

Reaction equation

HRID 2285910 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([O:20][C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[CH:23][CH:22]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>CO.[Pd]>[NH2:27][C:24]1[CH:23]=[CH:22][C:21]([O:20][C:11]2([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:12][CH2:13][N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:9][CH2:10]2)=[CH:26][CH:25]=1

Participants

5

Reactant 2

HCID 20536592HCID 20536592, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20542610HCID 20542610, compoundYield 22.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 1-benzyl-4-(4-nitrophenoxy)-4-phenylpiperidine (1.95 g, 5 mM), in methanol (100 ml) was hydrogenated over 5% Pd/C at atmospheric pressure and room temperature. After the theoretical uptake of hydrogen had occurred (about 2 hours), the catalyst was removed by filtration and the solvents removed under reduced pressure. Recrystallisation of the residue from IPA (twice) gave the title compound (400 mg), m.p. 124°-6° C.

Workup

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

Sources & evidence

ORD record
ord-086ede4270ef4ba3b311fbf25b93b274
Source dataset
uspto-grants-1982_04
Patent number
US04325953

Reaction notes

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