Ethanol → 4-[3-(1-Benzylpiperidin-4-yl)propanoyl]aniline

HRID 976146Notes

Reaction equation

HRID 976146 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11](/[CH:14]=[CH:15]/[C:16]([C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][CH:19]=2)=[O:17])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)C.[H][H]>[Pt]=O.C(O)(=O)C>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][C:16]([C:18]2[CH:19]=[CH:20][C:21]([NH2:24])=[CH:22][CH:23]=2)=[O:17])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 70279862(E)-4-[3-(1-benzylpiperidin-4-yl)propenoyl]nitrobenzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 199689194-[3-(1-Benzylpiperidin-4-yl)propanoyl]anilineYield 37.5%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

2.00 g of (E)-4-[3-(1-benzylpiperidin-4-yl)propenoyl]nitrobenzene was added to a mixed solvent of 30 ml of ethanol and 5 ml of acetic acid, and then 0.20 g of platinum oxide was added thereto. Thereafter, the mixture was stirred in a hydrogen stream at room temperature for 7.5 hours. After the reaction, the catalyst was removed by filtration, and the filtrate was condensed under reduced pressure. The obtained residue was applied to silica gel column chromatography to obtain 0.69 g of the title compound as pale yellow crystal.

Workup

  1. customAfter the reaction
  2. customthe catalyst was removed by filtration
  3. customcondensed under reduced pressure

Sources & evidence

ORD record
ord-ae05ad79f9eb4e99b49d5b851aab7b27
Source dataset
uspto-grants-1997_03
Patent number
US05610303

Reaction notes

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