Piperidine → HCID 12471526, compound

HRID 2051481Notes

Reaction equation

HRID 2051481 reaction equation
Br[C:2]1[CH:3]=[N+:4]([O-:15])[C:5]2[C:10]([C:11]=1[N+:12]([O-:14])=[O:13])=[CH:9][CH:8]=[CH:7][CH:6]=2.[NH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1>O1CCCC1>[N+:12]([C:11]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N+:4]([O-:15])=[CH:3][C:2]=1[N:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)([O-:14])=[O:13]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 84235Quinoline, 3-bromo-4-nitro-, 1-oxide

Product 1

HCID 12471526HCID 12471526, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Bromo-4-nitroquinoline-N-oxide (10 g, 0.037 mol) was dissolved in tetrahydrofuran (100 ml). To the solution, piperidine (7.9 g, 0.093 mol) was added and the mixture was stirred at room temperature until gradual crystallization occurred. Tetrahydrofuran was distilled off from the whole reaction mixture under vacuum and the residue was dissolved in chloroform. The chloroform layer was washed with water and dried with anhydrous sodium sulfate. After distilling off the chloroform under vacuum, the residue was washed with a small amount of ethanol and recovered by filtration under vacuum to obtain 4-nitro-3-piperidinoquinoline-N-oxide in an amount of 6.0 g (yield, 59%).

Workup

  1. distillationTetrahydrofuran was distilled off from the whole reaction mixture under vacuum
  2. dissolutionthe residue was dissolved in chloroform
  3. washThe chloroform layer was washed with water
  4. dry with materialdried with anhydrous sodium sulfate
  5. distillationAfter distilling off the chloroform under vacuum
  6. washthe residue was washed with a small amount of ethanol
  7. filtrationrecovered by filtration under vacuum

Sources & evidence

ORD record
ord-3b5c1d99455d418b9379f07dabe99adc
Source dataset
uspto-grants-1991_05
Patent number
US05019574

Reaction notes

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