Hydrochloric Acid → 3-(2-Methyl-3-piperidinopropionyl)-5-phenylisoxazole hydrochloride

HRID 1450656Notes

Reaction equation

HRID 1450656 reaction equation
C([C:9]1[CH:13]=[C:12]([C:14](=O)[CH2:15]C)O[N:10]=1)(=O)C1C=CC=CC=1.[C:18]([C:22]1[CH:26]=[C:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[O:24][N:23]=1)(=[O:21])[CH2:19][CH3:20].[ClH:33].N1CCCC[CH2:35]1.C=O.Cl>C(OCC)C.O1CCOCC1>[ClH:33].[CH3:20][CH:19]([CH2:35][N:10]1[CH2:15][CH2:14][CH2:12][CH2:13][CH2:9]1)[C:18]([C:22]1[CH:26]=[C:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[O:24][N:23]=1)=[O:21]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 2723721Piperidine, hydrochloride (1:1)HCID 126758503-Propionyl-5-phenylisoxazoleHCID 199769473-Benzoyl-5-propionylisoxazole

Product 1

HCID 199769033-(2-Methyl-3-piperidinopropionyl)-5-phenylisoxazole hydrochloride

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

To a mixture consisting of 1.5 g (7.5 mmol) of the ketone derivative, i.e., (3-propionyl-5-phenylisoxazole) prepared above in the procedure (3), 0.99 g (8.2 mmol) of piperidine hydrochloride, 0.36 g of paraformaldehyde and 3 ml of dioxane, 0.03 ml of 12N-hydrochloric acid was added. The resultant mixture was heated under reflux for 2 hours. After completion of the reaction, ethyl ether was added. Colorless crystals thus formed were collected by filtration and added to a saturated aqueous solution of sodium hydrogencarbonate. The solution was extracted with ethyl ether. The solvent was distilled off so that 3-(2-methyl-3-piperidinopropionyl)-5-phenylisoxazole was obtained as colorless crystals.

Workup

  1. additionwas added
  2. temperatureunder reflux for 2 hours
  3. additionwas added
  4. customColorless crystals thus formed
  5. filtrationwere collected by filtration
  6. additionadded to a saturated aqueous solution of sodium hydrogencarbonate
  7. extractionThe solution was extracted with ethyl ether
  8. distillationThe solvent was distilled off so that 3-(2-methyl-3-piperidinopropionyl)-5-phenylisoxazole
  9. customwas obtained as colorless crystals

Sources & evidence

ORD record
ord-5a61e2c4745c460eacc272b821585c0c
Source dataset
uspto-grants-1997_02
Patent number
US05602160

Reaction notes

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