Sodium Carbonate → HCID 57423903, compound

HRID 2064046Notes

Reaction equation

HRID 2064046 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][CH:9]([NH2:12])[CH2:8][CH2:7]1)=[O:5])[CH3:2].F[C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=1[N+:21]([O-:23])=[O:22].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O.O.C(OCC)(=O)C.[I-].[K+]>[F:20][C:18]1[CH:17]=[CH:16][C:15]([N+:21]([O-:23])=[O:22])=[C:14]([NH:12][CH:9]2[CH2:8][CH2:7][N:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:11][CH2:10]2)[CH:19]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 679672,4-DifluoronitrobenzeneHCID 100867Ethyl 4-amino-1-piperidinecarboxylate

Product 1

HCID 57423903HCID 57423903, compoundYield 86.2%

Reagents, catalysts & solvents 4

HCID 4875Potassium IodideCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

Ethyl-4-amino-1-piperidine-carboxylate (11.9 g, 69 mmol) was added to a stirred suspension of 2,4-difluoronitrobenzene (10.0 g, 63 mmol), sodium carbonate (6.7 g, 63 mmol) and potassium iodide (0.1 g, 0.6 mmol) in dimethylformamide (100 mL). The mixture was heated to 50° C., stirred for 5 hours and then allowed to cool. The reaction mixture was diluted with water (130 mL) and ethyl acetate (200 mL). The organic phase was separated and the aqueous phase was extracted with ethyl acetate (2×200 mL). The organic extracts were combined, extracted with a 10% aqueous solution of citric acid (250 mL), dried over MgSO4 and evaporated under reduced pressure. The residue was purified by column chromatography on silica, eluting with ethyl acetate/hexane (1:2) to give the title compound (16.9 g, 86% yield) as a yellow solid. (Rf: 0.5 (ethyl acetate/hexane 7:8))

Workup

  1. temperatureto cool
  2. customThe organic phase was separated
  3. extractionthe aqueous phase was extracted with ethyl acetate (2×200 mL)
  4. extractionextracted with a 10% aqueous solution of citric acid (250 mL)
  5. dry with materialdried over MgSO4
  6. customevaporated under reduced pressure
  7. customThe residue was purified by column chromatography on silica
  8. washeluting with ethyl acetate/hexane (1:2)

Sources & evidence

ORD record
ord-1471dae80c294105805b915a3c991011
Source dataset
uspto-grants-2012_10
Patent number
US08288413B2

Reaction notes

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