Sodium Carbonate → HCID 59565532, compound

HRID 2064060Notes

Reaction equation

HRID 2064060 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].Cl[C:14]1[CH:15]=[C:16]([C:23]([F:26])([F:25])[F:24])[CH:17]=[CH:18][C:19]=1[N+:20]([O-:22])=[O:21].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O.O.C(OCC)(=O)C.[I-].[K+]>[N+:20]([C:19]1[CH:14]=[CH:15][C:16]([C:23]([F:24])([F:25])[F:26])=[CH:17][C:18]=1[NH:12][CH:9]1[CH2:8][CH2:7][N:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:11][CH2:10]1)([O-:22])=[O:21]

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 100867Ethyl 4-amino-1-piperidinecarboxylateHCID 1645942-Chloro-1-nitro-4-(trifluoromethyl)benzene

Product 1

HCID 59565532HCID 59565532, compoundYield 40%

Reagents, catalysts & solvents 4

HCID 4875Potassium IodideCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

Ethyl-4-amino-1-piperidine-carboxylate (16.0 g, 92 mmol) was added to a stirred suspension of 3-chloro-4-nitrobenzotrifluoride (19.0 g, 84 mmol), sodium carbonate (8.9 g, 84 mmol) and potassium iodide (0.14 g, 0.84 mmol) in dimethylformamide (200 mL). The mixture was heated to 90° 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 aqueous phase was separated and the organic phase was extracted with water (2×200 mL). The organic phase was dried over MgSO4 and evaporated under reduced pressure. The residue was purified by column chromatography on silica, eluting with ethyl acetate/hexane (1:5) to give the title compound (12.0 g, 40% yield) as an orange solid. (Rf: 0.4 (ethyl acetate/hexane 1:5))

Workup

  1. temperatureto cool
  2. customThe aqueous phase was separated
  3. extractionthe organic phase was extracted with water (2×200 mL)
  4. dry with materialThe organic phase was dried over MgSO4
  5. customevaporated under reduced pressure
  6. customThe residue was purified by column chromatography on silica
  7. washeluting with ethyl acetate/hexane (1:5)

Sources & evidence

ORD record
ord-5d823c36d925495b8ae5ed7d7161842d
Source dataset
uspto-grants-2012_10
Patent number
US08288413B2

Reaction notes

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