1-{3-[1-(3-Fluorophenyl)methylidene]piperidin-1-yl}ethanone → 1-[3-(3-Fluorobenzyl)piperidin-1-yl]ethanone

HRID 928077Notes

Reaction equation

HRID 928077 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]2[CH2:14][CH2:13][CH2:12][N:11]([C:15](=[O:17])[CH3:16])[CH2:10]2)[CH:5]=[CH:6][CH:7]=1>C(OCC)(=O)C.[OH-].[Pd+2].[OH-]>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[CH2:8][CH:9]1[CH2:14][CH2:13][CH2:12][N:11]([C:15](=[O:17])[CH3:16])[CH2:10]1

Participants

4

Reactant 1

HCID 709845881-{3-[1-(3-Fluorophenyl)methylidene]piperidin-1-yl}ethanone2×

Product 1

HCID 710069491-[3-(3-Fluorobenzyl)piperidin-1-yl]ethanoneYield 93.5%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-{3-[1-(3-fluorophenyl)methylidene]piperidin-1-yl}ethanone (Intermediate 225, 0.7 g), palladium hydroxide (20% on carbon, 0.07 g) in ethyl acetate (20 mL) and IMS (1 mL) was degassed by nitrogen/vacuum purging. The mixture was stirred under an atmosphere of hydrogen for 21.5 hours. The mixture was filtered the filtrate was evaporated to dryness to give 1-[3-(3-fluorobenzyl)piperidin-1-yl]ethanone (0.66 g).

Workup

  1. customwas degassed by nitrogen/vacuum
  2. custompurging
  3. filtrationThe mixture was filtered the filtrate
  4. customwas evaporated to dryness

Sources & evidence

ORD record
ord-14591381bba54e90b03e8659e1ec164c
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Reaction notes

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