Sodium Carbonate → tert-Butyl 4-(5-nitropyridine-2-ylamino)piperidine-1-carboxylate

HRID 1993669Notes

Reaction equation

HRID 1993669 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH2:14])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(=O)([O-])[O-].[Na+].[Na+].Cl[C:22]1[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][N:23]=1>C(O)C>[C:4]([O:3][C:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:22]2[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][N:23]=2)[CH2:10][CH2:9]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 783082-Chloro-5-nitropyridineHCID 12682914-Amino-1-Boc-piperidine

Product 1

HCID 53255493tert-Butyl 4-(5-nitropyridine-2-ylamino)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Dissolve N-Boc-4-aminopiperidine (0.9 g, 4.8 mmol) in dry ethanol and add solid sodium carbonate (0.8 g, 7.9 mmol) at 0° C., followed by 2-chloro-5-nitro-pyridine (0.6 g, 3.9 mmol). Stir the solution at room temperature overnight, then heat the solution at 9° C. for 6 hours. Stir at room temperature overnight. Evaporate the solvent under reduced pressure and partition the crude mixture between EtOH and water. Extract with EtOAc and wash the organic layer with saturated aq. sodium chloride solution. Combine organic layers and dry over MgSO4. Filter and evaporate the solvent in order to obtain 4-(5-Nitro-pyridin-2-ylamino)-piperidine-1-carboxylic acid tert-butyl ester.

Workup

  1. temperatureheat the solution at 9° C. for 6 hours
  2. stirringStir at room temperature overnight
  3. customEvaporate the solvent under reduced pressure
  4. custompartition the crude mixture between EtOH and water
  5. extractionExtract with EtOAc
  6. washwash the organic layer with saturated aq. sodium chloride solution
  7. dry with materialCombine organic layers and dry over MgSO4
  8. filtrationFilter
  9. customevaporate the solvent in order

Sources & evidence

ORD record
ord-5889c8e2a7d948fdb556c226a1f8094e
Source dataset
uspto-grants-2010_01
Patent number
US07652015B2

Reaction notes

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