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

HRID 1449731Notes

Reaction equation

HRID 1449731 reaction equation
FC(F)(F)C(O)=O.CC(C)(O[N:12]1[CH2:17][CH2:16][CH:15]([N:18]([CH3:28])[C:19]2[C:24]([N+:25]([O-:27])=[O:26])=[CH:23][CH:22]=[CH:21][N:20]=2)[CH2:14][C:13]1=C=O)C.[OH-].[Na+]>C(Cl)Cl>[CH3:28][N:18]([CH:15]1[CH2:16][CH2:17][NH:12][CH2:13][CH2:14]1)[C:19]1[C:24]([N+:25]([O-:27])=[O:26])=[CH:23][CH:22]=[CH:21][N:20]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 86750273(1,1-dimethylethoxy)-carbonyl-4-(N-methyl-N-(3-nitro-2-pyridinyl)amino)piperidine

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-d5f68127f62d48b1a0b97df61ea82e53
Source dataset
uspto-grants-1997_02
Patent number
US05599930

Reaction notes

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