tert-Butyl 4-(3-fluoro-4-methoxybenzylidene)piperidine-1-carboxylate → HCID 69354983, compound

HRID 495446Notes

Reaction equation

HRID 495446 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[CH:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([F:23])[CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([F:23])[CH:16]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 2

HCID 69356823tert-Butyl 4-(3-fluoro-4-methoxybenzylidene)piperidine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 69354983HCID 69354983, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 4-(3-fluoro-4-methoxy-benzylidene)-piperidine-1-carboxylic acid tert-butyl ester (4.7 g, 14.6 mmol) in methanol (400 mL) was allowed to stir under atmospheric pressure of hydrogen at room temperature in the presence of 10% palladium on carbon (0.8 g) for 16 hours. Removal of the catalyst by filtration and evaporation of the filtrate gave a crude oil. Silica gel chromatography eluting with ethyl acetate in hexane (10%) gave the title compound (4.3 g, 99%) as a colourless oil.

Workup

  1. customRemoval of the catalyst
  2. filtrationby filtration and evaporation of the filtrate
  3. customgave a crude oil
  4. washSilica gel chromatography eluting with ethyl acetate in hexane (10%)

Sources & evidence

ORD record
ord-e9bc15d1ce524b47b1cd62614dc5ee10
Source dataset
uspto-grants-2005_09
Patent number
US06939871B2

Reaction notes

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