Potassium Hydroxide → O-(2-piperidinoethyl)-3-pyridinehydroximoyl chloride hydrochloride

HRID 580890

Reaction equation

HRID 580890 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([NH2:9])=N)[CH:2]=1.[ClH:10].[Cl:11][CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.[OH-:20].[K+]>C(O)C>[ClH:11].[N:14]1([CH2:13][CH2:12][O:20][N:9]=[C:7]([Cl:10])[C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 74826Piperidine, 1-(2-chloroethyl)-, hydrochlorideHCID 2020433-Pyridinecarboxamidine

Product 1

HCID 86754158O-(2-piperidinoethyl)-3-pyridinehydroximoyl chloride hydrochlorideYield 23.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

After dissolving 6.45 g (47.0 mmoles) of 3-pyridinecarboxamidine in 120.4 ml of 0.83N potassium hydroxide solution in ethanol under stirring, 8.65 g (47.0 mmoles) of 1-(2-chloroethyl)piperidine hydrochloride are added under stirring, then the reaction mixture is boiled under reflux for 4 hours. The precipitated potassium chloride is filtered off, the filtrate is clarified by activated carbon and evaporated. The residue is dissolved in 100 ml of chloroform, and the organic solution is washed 3 times with 100 ml of 1N sodium hydroxide solution each, then with 50 ml of water. The organic phase is dried over sodium sulfate and evaporated. The residue is purified by column chromatography (adsorbent: recrystallized from ether to give 2.69 g (23.5%) of the aimed product, m. p.: 81-83° C. (from ether).

Workup

  1. stirringunder stirring
  2. temperatureunder reflux for 4 hours
  3. filtrationThe precipitated potassium chloride is filtered off
  4. customevaporated
  5. dissolutionThe residue is dissolved in 100 ml of chloroform
  6. washthe organic solution is washed 3 times with 100 ml of 1N sodium hydroxide solution each, then with 50 ml of water
  7. dry with materialThe organic phase is dried over sodium sulfate
  8. customevaporated
  9. customThe residue is purified by column chromatography (adsorbent
  10. customrecrystallized from ether

Sources & evidence

ORD record
ord-2c1413ce3f0b41d98b12e6d072763aa8
Source dataset
uspto-grants-1999_07
Patent number
US05919796

Linked notes

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