HCID 18381945, compound → HCID 18381929, compound

HRID 2297526Notes

Reaction equation

HRID 2297526 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([N:10]2[CH2:15][CH2:14][CH:13]([CH:16]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:12][CH2:11]2)[CH:7]=[CH:8][CH:9]=1)([O-])=O>C(O)C.[Pd]>[C:23]1([CH:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:13]2[CH2:12][CH2:11][N:10]([C:6]3[CH:5]=[C:4]([NH2:1])[CH:9]=[CH:8][CH:7]=3)[CH2:15][CH2:14]2)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

4

Reactant 1

HCID 18381945HCID 18381945, compound

Product 1

HCID 18381929HCID 18381929, compoundYield 90.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1-(3-nitrophenyl)-4-(diphenylmethyl)piperidine (854 mg) was dissolved in ethanol (60 ml), and 10% palladium/carbon (76 mg) was added thereto, followed by stirring the mixture overnight under hydrogen atmosphere. Palladium/carbon was removed by filtration through Celite and the filtrate was concentrated, followed by purifying the residue by silica gel column chromatography (hexane:ethyl acetate=5:4) to obtain 711 mg of 3-(4-(diphenylmethyl)piperidyl)phenylamine. Yield: 90%.

Workup

  1. customPalladium/carbon was removed by filtration through Celite
  2. concentrationthe filtrate was concentrated
  3. customby purifying the residue by silica gel column chromatography (hexane:ethyl acetate=5:4)

Sources & evidence

ORD record
ord-b0324e4c72fc4c6e970a830545ebdb05
Source dataset
uspto-grants-2002_12
Patent number
US06492364B1

Reaction notes

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