Acetic Acid → HCID 14553815, compound

HRID 1904281Notes

Reaction equation

HRID 1904281 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH2:14][CH:15]([CH3:26])[CH2:16][N:17]2[CH2:22][CH2:21][CH:20]=[C:19]([CH2:23][O:24][CH3:25])[CH2:18]2)[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C>C(O)C.[C].[Pd]>[O:1]([C:8]1[CH:9]=[C:10]([CH2:14][CH:15]([CH3:26])[CH2:16][N:17]2[CH2:22][CH2:21][CH2:20][CH:19]([CH2:23][O:24][CH3:25])[CH2:18]2)[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 14553814HCID 14553814, compound

Product 1

HCID 14553815HCID 14553815, compoundYield 94.5%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

N-[3-(m-Phenoxyphenyl)-2-methylpropyl]-3-methoxymethyl-1,2,5,6-tetrahydropyridine (0.2 g) was dissolved in ethanol (20 ml), followed by addition of acetic acid (1 ml) thereto. To the resultant mixture, 5% palladium-carbon (0.2 g) was added at room temperature under nitrogen stream, and then hydrogenation was carried out under nitrogen stream. After absorption of hydrogen was completed, the catalyst was removed by filtration, and the filtrate was combined with 15% aqueous sodium hydroxide solution (20 ml) and extracted with diethyl ether. The ether extract was washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography to give N-[3-(m-phenoxyphenyl)-2-methylpropyl]-3-methoxymethylpiperidine (0.19 g).

Workup

  1. customAfter absorption of hydrogen
  2. customthe catalyst was removed by filtration
  3. extractionextracted with diethyl ether
  4. extractionThe ether extract
  5. washwas washed with saturated aqueous sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-a5765714c61242b299f0124502441b64
Source dataset
uspto-grants-1989_06
Patent number
US04837236

Reaction notes

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