Trifluoroacetic acid → 4-(N-methyl-N-(3-nitro-2-pyridinyl)amino)piperidine

HRID 2293761Notes

Reaction equation

HRID 2293761 reaction equation
FC(F)(F)C(O)=O.CC(C)(OC([N:14]1[CH2:19][CH2:18][CH:17]([N:20]([CH3:30])[C:21]2[C:26]([N+:27]([O-:29])=[O:28])=[CH:25][CH:24]=[CH:23][N:22]=2)[CH2:16][CH2:15]1)=O)C.[OH-].[Na+]>C(Cl)Cl>[CH3:30][N:20]([CH:17]1[CH2:18][CH2:19][NH:14][CH2:15][CH2:16]1)[C:21]1[C:26]([N+:27]([O-:29])=[O:28])=[CH:25][CH:24]=[CH:23][N:22]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 54208510tert-Butyl 4-(methyl(3-nitropyridin-2-yl)amino)piperidine-1-carboxylate

Product 1

HCID 214776804-(N-methyl-N-(3-nitro-2-pyridinyl)amino)piperidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (13.0 ml) is added to a solution of 1-((1,1-dimethylethoxy)-carbonyl)-4-(N-methyl-N-(3-nitro-2-pyridinyl)amino)piperidine (PREPARATION 49) in methylene chloride (100 ml) with cooling to -78°. The mixture is warmed to 20°-25°, stirred 17 hrs, cooled to 0° and basified to pH 12 with 5% sodium hydroxide. The phases are separated and the aqueous phase is extracted with methylene chloride (2×50 ml). The combined organic phases are dried over sodium sulfate and concentrated to give the title compound, mp 115.5°-117°.

Workup

  1. temperaturewith cooling to -78°
  2. temperatureThe mixture is warmed to 20°-25°
  3. customThe phases are separated
  4. extractionthe aqueous phase is extracted with methylene chloride (2×50 ml)
  5. dry with materialThe combined organic phases are dried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e22d158864564f90ad898758872bafad
Source dataset
uspto-grants-1997_11
Patent number
US05686610

Reaction notes

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