Potassium Carbonate → HCID 68509534, compound

HRID 1716591Notes

Reaction equation

HRID 1716591 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH3:11])[CH:7]=[CH:8][C:9]=1F)([O-:3])=[O:2].[NH2:12][CH:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[C:22]([O:21][C:19]([N:16]1[CH2:17][CH2:18][CH:13]([NH:12][C:9]2[CH:8]=[CH:7][C:6]([CH3:11])=[CH:5][C:4]=2[N+:1]([O-:3])=[O:2])[CH2:14][CH2:15]1)=[O:20])([CH3:25])([CH3:23])[CH3:24]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1362874-Fluoro-3-nitrotolueneHCID 12682914-Amino-1-Boc-piperidine

Product 1

HCID 68509534HCID 68509534, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

To a 100 mL round bottom flask was added 3-nitro-4-fluorotoluene (1.55 g, 10 mmol), 4-amino-1-N-Boc-piperidine (2.40 g, 12 mmol), powder K2CO3 (2.76 g, 20 mmol) and dry DMF (30 mL). The mixture was stirred at 85° C. overnight. Solvents were evaporated under reduced pressure. The residue was extracted with ethyl acetate and the combined organic layers were washed with brine. The organic layer was dried over Na2SO4 and filtered. Removal of solvents under reduced pressure gave an oil residue. 4-(4-methyl-2-nitrophenylamino)-piperidine-1-carboxylic acid tert-butyl ester was isolated as a solid (3.13 g, 94%) from Biotage flash column chromatography using hexanes and ethyl acetate (3/1 ratio).

Workup

  1. customSolvents were evaporated under reduced pressure
  2. extractionThe residue was extracted with ethyl acetate
  3. washthe combined organic layers were washed with brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. customRemoval of solvents under reduced pressure
  7. customgave an oil residue

Sources & evidence

ORD record
ord-6b41f6759c674283ac0d42738c30552b
Source dataset
uspto-grants-2010_09
Patent number
US07803816B2

Reaction notes

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