Piperidine → HCID 21548172, compound

HRID 1604907Notes

Reaction equation

HRID 1604907 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[N+:3]=1[O-:9].[NH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1>C1C=CC=CC=1>[Cl:8][C:4]1[N+:3]([O-:9])=[C:2]([N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 8082Piperidine2×HCID 8176732,6-Dichloropyridine N-Oxide

Product 1

HCID 21548172HCID 21548172, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution was prepared by dissolving 10 grams (0.061 mole) of 2,6-dichloropyridine-N-oxide in 100 milliliters of benzene at 35 C. To this solution was added dropwise 10.3 grams (0.122 mole) of piperidine. Upon completion of the piperidine addition, the reaction mixture was refluxed for 2 hours. At the completion of the reaction, the insoluble material contained in the reaction mixture was removed by filtration and benzene thereafter distilled off. The oily residue which remained was taken up in hexane. The 6-chloro-2-(piperidino)pyridine-N-oxide product was recovered by recrystallization from hexane and recovered in a yield of 7.5 grams. The product melted at 38°-41°C. and was found upon analysis to have carbon, hydrogen, chlorine and nitrogen contents of 54.5, 5.9, 19.9 and 12.9 percent, respectively, as compared with the theoretical contents of 56.8, 6.1, 16.7 and 13.2 percent, respectively, calculated for the above named compound.

Workup

  1. customA solution was prepared
  2. temperaturethe reaction mixture was refluxed for 2 hours
  3. customAt the completion of the reaction
  4. customwas removed by filtration and benzene
  5. distillationthereafter distilled off
  6. customThe 6-chloro-2-(piperidino)pyridine-N-oxide product was recovered by recrystallization from hexane
  7. customrecovered in a yield of 7.5 grams

Sources & evidence

ORD record
ord-dc7d145403ea4e9aa0ef9f0adc482193
Source dataset
uspto-grants-1976_04
Patent number
US03948910

Reaction notes

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