Piperidine → Piperidine, 5-nitro-2-pyridyl-

HRID 400578Notes

Reaction equation

HRID 400578 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[NH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1>C1COCC1.O.C(OCC)C>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[N:3][CH:4]=1)([O-:10])=[O:9]

Participants

6

Reactant 2

HCID 8082PiperidineHCID 783082-Chloro-5-nitropyridine

Product 1

HCID 97158Piperidine, 5-nitro-2-pyridyl-

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-Chloro-5-nitropyridine (10 g, 63.3 mmol) was dissolved in 150 mL of THF. 20 mL of piperidine was then added and the resulting mixture was stirred for 18 hours at room temperature. The reaction mixture with copious precipitate was then diluted with 200 mL of water and 100 mL of diethyl ether. The layers were thoroughly mixed and separated. The organic layer was dried over sodium sulfate and concentrated in vacuo. The bright yellow solid was redissolved in 35 mL of dichloromethane and, with vigorous stirring, hexanes were added until the product began to precipitate. The bright yellow solid was collected by filtration and dried to afford 12.5 g of 5′-nitro-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl.

Workup

  1. additionThe layers were thoroughly mixed
  2. customseparated
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. dissolutionThe bright yellow solid was redissolved in 35 mL of dichloromethane and, with vigorous stirring, hexanes
  6. additionwere added until the product
  7. customto precipitate
  8. filtrationThe bright yellow solid was collected by filtration
  9. customdried

Sources & evidence

ORD record
ord-c5bdac3e8b2647528994cbaf535ac93c
Source dataset
uspto-grants-2014_06
Patent number
US08741897B2

Reaction notes

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