2-Piperidone → HCID 20763734, compound

HRID 1436864Notes

Reaction equation

HRID 1436864 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[CH:4][CH:3]=1.[NH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][C:11]1=[O:16].[H-].[Na+]>CN(C=O)C>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][C:11]2=[O:16])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 126652-PiperidoneHCID 24758Sodium hydrideHCID 680214-Fluorobenzyl bromide

Product 1

HCID 20763734HCID 20763734, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-fluorobenzyl bromide (15 g, 79 mmol) and 2-piperidinone (8.4 g, 85 mmol) in DMF (150 mL) was added sodium hydride (3.6 g of a 60% suspension in mineral oil, 90 mmol) in portions over a period of 20 min. The mixture was stirred at ambient temperature for 18 hours. The solvent was removed under vacuum and the residue was partitioned between EtOAc and water. The organic extract was washed with brine, dried over MgSO4, filtered, and concentrated under vacuum. The residual oil was purified using silica gel column chromatography eluting with 50%-70% ethyl acetate in hexanes. The appropriate fractions were combined and concentrated to afford the title compound as white solid. 1H NMR (400 MHz, CDCl3) δ 7.23 (dd, J=8.7; 5.4 Hz, 2H), 7.00 (t, J=8.7 Hz, 2H), 4.56 (s, 2H), 3.18 (t, J=6 Hz, 2H), 2.46 (t, J=6 Hz, 2H), 1.79 (m, 4H).

Workup

  1. customThe solvent was removed under vacuum
  2. customthe residue was partitioned between EtOAc and water
  3. extractionThe organic extract
  4. washwas washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customThe residual oil was purified
  9. washeluting with 50%-70% ethyl acetate in hexanes
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-040caeedad604acd8fd1974f785ee830
Source dataset
uspto-grants-2009_11
Patent number
US07619086B2

Reaction notes

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