Piperidine → HCID 13557174, compound

HRID 980207Notes

Reaction equation

HRID 980207 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:7]([C:9]1[O:13][N:12]=[CH:11][C:10]=1[C:14](Cl)=[O:15])[CH3:8]>C(#N)C.C(Cl)Cl>[CH2:7]([C:9]1[O:13][N:12]=[CH:11][C:10]=1[C:14]([N:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)=[O:15])[CH3:8]

Participants

5

Reactant 2

HCID 8082PiperidineHCID 194398045-Ethyl-1,2-oxazole-4-carbonyl chloride

Product 1

HCID 13557174HCID 13557174, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

0.2 mol (17.0 g) of piperidine is added dropwise to 0.1 mol (16.0 g) of 5-ethyl-4-isoxazolecarboxylic acid chloride dissolved in 200 ml of acetonitrile, at room temperature with stirring. Stirring is continued for 20 minutes and the mixture is then cooled to room temperature and the piperidine hydrochloride precipitated is filtered off with suction. The filtrate is concentrated under reduced pressure. An oily residue is obtained, and is taken up in 200 ml of methylene chloride, and the mixture is washed first with 100 ml of 2N hydrochloric acid and then with water. After drying over sodium sulfate, the mixture is concentrated under reduced pressure and the oily residue is distilled under reduced pressure (bulb tube distillation). N-(5-Ethyl-4-isoxazolylcarbonyl)-piperidine of boiling point (7 mbar) 90°-110° C. is thus obtained.

Workup

  1. stirringStirring
  2. customthe piperidine hydrochloride precipitated
  3. filtrationis filtered off with suction
  4. concentrationThe filtrate is concentrated under reduced pressure
  5. customAn oily residue is obtained
  6. washthe mixture is washed first with 100 ml of 2N hydrochloric acid
  7. dry with materialAfter drying over sodium sulfate
  8. concentrationthe mixture is concentrated under reduced pressure
  9. distillationthe oily residue is distilled under reduced pressure (bulb tube distillation)

Sources & evidence

ORD record
ord-fecab3df499b4b7ab77ad2c069f2b6d7
Source dataset
uspto-grants-1987_01
Patent number
US04636513

Reaction notes

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