Ethanol → Methyl 1-(2-phenylethyl)-1,4,5,6-tetrahydro-3-pyridyl ketone

HRID 359317Notes

Reaction equation

HRID 359317 reaction equation
[Br-].[C:2]1([CH2:8][CH2:9][N+:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16](=[O:18])[CH3:17])[CH:11]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.C(O)C>[Pd]>[C:2]1([CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][CH2:13][C:12]([C:16]([CH3:17])=[O:18])=[CH:11]2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 8471TriethylamineHCID 189633921-(2-Phenylethyl)-3-acetylpyridinium bromide

Product 1

HCID 18963355Methyl 1-(2-phenylethyl)-1,4,5,6-tetrahydro-3-pyridyl ketone

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A solution of 1-(2-phenylethyl)-3-acetylpyridinium bromide (30.6 g, 0.1 mole) and triethylamine (10.1 g, 0.1 mole) in ethyl alcohol (50 mole) over 5% palladium on carbon (5 g) was hydrogenated at room temperature and pressure. Upon cessation of hydrogen uptake, the catalyst was filtered and the filtrate concentrated at reduced pressure. The semi-solid filtered and the filtrate concentrated under reduced pressure to leave a pale brown oil, methyl 1-(2-phenyl ethyl)-1,4,5,6-tetrahydro-3-pyridyl ketone (6).

Workup

  1. customwas hydrogenated at room temperature
  2. filtrationUpon cessation of hydrogen uptake, the catalyst was filtered
  3. concentrationthe filtrate concentrated at reduced pressure
  4. filtrationThe semi-solid filtered
  5. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-783cbb81c9b448d59e5bb8b2b3696832
Source dataset
uspto-grants-1991_03
Patent number
US05000946

Reaction notes

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