Piperidine → HCID 22261701, compound

HRID 1610219Notes

Reaction equation

HRID 1610219 reaction equation
[C:1]([CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:5])[CH:2]([CH3:4])[CH3:3].[F:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]=[C:20]([N+]([O-])=O)[CH3:21])=[CH:15][CH:14]=1.N1CCCCC1>C(O)C>[F:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:1]([CH:2]([CH3:4])[CH3:3])[O:5][C:20]=2[CH3:21])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 130531-Fluoro-4-(2-nitro-1-propen-1-yl)benzeneHCID 81583Ethyl isobutyrylacetate

Product 1

HCID 22261701HCID 22261701, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of ethyl isobutyrylacetate (20.06 g, 126.8 mmol) and 1-fluoro-4-(2-nitro-1-propenyl)benzene (23.0 g, 127 mmol) in ethanol (100 ml) was added piperidine (12.5 ml, 127 mmol) at room temperature, and the mixture was stirred overnight at room temperature and at 80° C. for 1 hr. The solvent of the reaction solution was evaporated under-reduced pressure, water (50 ml) and conc. hydrochloric acid (30 ml) were added to the residue, and the mixture was stirred at room temperature for 1 hr. The reaction solution was extracted twice with ethyl acetate and the collected organic layer was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=20/1) to give the objective substance.

Workup

  1. customThe solvent of the reaction solution was evaporated under-reduced pressure, water (50 ml) and conc. hydrochloric acid (30 ml)
  2. additionwere added to the residue
  3. stirringthe mixture was stirred at room temperature for 1 hr
  4. extractionThe reaction solution was extracted twice with ethyl acetate
  5. dry with materialthe collected organic layer was dried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=20/1)
  8. customto give the objective substance

Sources & evidence

ORD record
ord-0fc6de898b2940d29e916c35cc460f05
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

Loading…