Benzyl 4-(3-fluorobenzylidene)piperidine-1-carboxylate → 4-[(3-Fluorophenyl)methyl]piperidine

HRID 928047Notes

Reaction equation

HRID 928047 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=1)[CH:5]=[C:6]1[CH2:11][CH2:10][N:9](C(OCC2C=CC=CC=2)=O)[CH2:8][CH2:7]1>[OH-].[OH-].[Pd+2].C(O)(=O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=1)[CH2:5][CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1

Participants

4

Reactant 1

HCID 70984044Benzyl 4-(3-fluorobenzylidene)piperidine-1-carboxylate2×

Product 1

HCID 107281414-[(3-Fluorophenyl)methyl]piperidineYield 85.3%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of benzyl 4-(3-fluorobenzylidene)piperidine-1-carboxylate (Intermediate 181, 1.05 g), 20% palladium hydroxide on carbon (0.227 g), IMS (30 mL) and acetic acid (10 mL) was degassed by nitrogen/vacuum purging. The mixture was placed under an atmosphere of hydrogen with rapid stirring. After 2 hours the mixture was filtered and the filtrate was diluted with water (40 mL) and neutralized with Na2CO3. The solution was saturated with sodium chloride, extracted with ethyl acetate dried (MgSO4) and filtered. The filtrate was concentrated in vacuo and the residue was dissolved in a mixture of methanol and water (20 mL, 1:1) and passed down a SCX-2 column. The product was eluted with 2M ammonia to give 4-(3-fluorobenzyl)piperidine (0.532 g)

Workup

  1. customwas degassed by nitrogen/vacuum
  2. custompurging
  3. filtrationAfter 2 hours the mixture was filtered
  4. additionthe filtrate was diluted with water (40 mL)
  5. extractionextracted with ethyl acetate
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated in vacuo
  9. dissolutionthe residue was dissolved in a mixture of methanol and water (20 mL, 1:1)
  10. washThe product was eluted with 2M ammonia

Sources & evidence

ORD record
ord-36ee5cd19577485f80c6360881a56c36
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Reaction notes

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