Sodium Carbonate → HCID 57423906, compound

HRID 2064058Notes

Reaction equation

HRID 2064058 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:15]=[C:16]([CH3:23])[CH:17]=[CH:18][C:19]=1[N+:20]([O-:22])=[O:21].C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C.CCCCCC>CN(C)C=O.O.C(OCC)(=O)C.[I-].[K+]>[CH3:23][C:16]1[CH:15]=[CH:14][C:19]([N+:20]([O-:22])=[O:21])=[C:18]([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:17]=1

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 67966Benzene, 2-fluoro-4-methyl-1-nitro-HCID 100867Ethyl 4-amino-1-piperidinecarboxylateHCID 21226206Ethyl acetate hexane

Product 1

HCID 57423906HCID 57423906, compoundYield 84%

Reagents, catalysts & solvents 4

HCID 4875Potassium IodideCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

Ethyl-4-amino-1-piperidine-carboxylate (18.3 g, 106 mmol) was added to a stirred suspension of 3-fluoro-4-nitrotoluene (15.0 g, 97 mmol), sodium carbonate (10.3 g, 97 mmol) and potassium iodide (0.16 g, 0.97 mmol) in dimethylformamide (150 mL). The mixture was heated to 50° C., stirred for 15 hours and then allowed to cool. The reaction mixture was diluted with water (200 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 dichloromethane and then ethyl acetate/hexane (7:8) to give the title compound (25.0 g, 84% yield) as a yellow solid. (Rf: 0.3 (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 dichloromethane

Sources & evidence

ORD record
ord-15f70ff8de18495bad1e467ca0bce737
Source dataset
uspto-grants-2012_10
Patent number
US08288413B2

Reaction notes

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