HCID 58218878, compound → 1-[4-[(1-Methyl-4-piperidinyl)methyl]phenyl]ethanone

HRID 885842Notes

Reaction equation

HRID 885842 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5](=[CH:8][C:9]2[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[CH:11][CH:10]=2)[CH2:4][CH2:3]1>CCO.[Pd]>[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([C:15](=[O:17])[CH3:16])=[CH:13][CH:14]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 58218878HCID 58218878, compound

Product 1

HCID 582083431-[4-[(1-Methyl-4-piperidinyl)methyl]phenyl]ethanoneYield 105.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1-[4-(1-methyl-piperidin-4-ylidenemethyl)-phenyl]-ethanone (401 mg, 1.75 mmol) was dissolved in EtOH (20 ml) and 5% Pd/C (40 mg) was added to the resulting solution. The mixture was hydrogenated in a Parr apparatus at 40 psi for 2 h. The catalyst was then filtered and the solvent was removed in vacuo. The residue was taken up with DCM and treated with HCl/Et2O until reaching a pH value of 1. The solvent was removed in vacuo to give an oil which was allowed to crystallize. The solid was triturated in Et2O and filtered to obtain 426 mg of 1-[4-(1-methyl-piperidin-4-ylmethyl)-phenyl]-ethanone as its hydrochloride salt.

Workup

  1. filtrationThe catalyst was then filtered
  2. customthe solvent was removed in vacuo
  3. additiontreated with HCl/Et2O
  4. customThe solvent was removed in vacuo
  5. customto give an oil which
  6. customto crystallize
  7. customThe solid was triturated in Et2O
  8. filtrationfiltered

Sources & evidence

ORD record
ord-2d3a8394c3fa42e3b17a44e2d6a24a38
Source dataset
uspto-grants-2012_08
Patent number
US08242175B2

Reaction notes

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