Piperidine → HCID 53823551, compound

HRID 249471Notes

Reaction equation

HRID 249471 reaction equation
[CH3:1][S:2][C:3](SC)=[CH:4][N+:5]([O-:7])=[O:6].[NH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1>CCO>[CH3:1][S:2][C:3]([N:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)=[CH:4][N+:5]([O-:7])=[O:6]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 836231,1-Bis(methylthio)-2-nitroethylene

Product 1

HCID 53823551HCID 53823551, compoundYield 39.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

In 20 ml of EtOH was dissolved 1.7 g (0.01 mole) of 1,1-bis(methylthio)-2-nitroethylene under heating and 0.9 g (0.01 mole) of piperidine dissolved in 10 ml of EtOH was added dropwise in 3 portions at 30-minutes intervals under reflux. After 2 hours of reflux, the solvent was distilled off and the residue was chromatographed on a silica gel column and eluted with AcOEt-toluene (2:3). The above procedure yielded 0.8 g of the title compound as yellow prisms.

Workup

  1. temperatureunder heating
  2. additionwas added dropwise in 3 portions at 30-minutes intervals
  3. temperatureunder reflux
  4. temperatureAfter 2 hours of reflux
  5. distillationthe solvent was distilled off
  6. customthe residue was chromatographed on a silica gel column
  7. washeluted with AcOEt-toluene (2:3)

Sources & evidence

ORD record
ord-053be33348894c8391f2a3bae547bc01
Source dataset
uspto-grants-1993_05
Patent number
US05214152

Reaction notes

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