Hydrochloric Acid → HCID 19976911, compound

HRID 1440347Notes

Reaction equation

HRID 1440347 reaction equation
[C:1]1([C:7]2[C:11]([C:12](=[O:15])[CH2:13][CH3:14])=[C:10]([CH3:16])[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[NH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.[CH2:24]=O.Cl>C(OCC)C.O.O1CCOCC1>[C:1]1([C:7]2[C:11]([C:12](=[O:15])[CH:13]([CH3:24])[CH2:14][N:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)=[C:10]([CH3:16])[O:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 2723721Piperidine, hydrochloride (1:1)HCID 19976909HCID 19976909, compound

Product 1

HCID 19976911HCID 19976911, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

Added to 3 ml of dioxane were 2.0 g (9.3 mmol) of 3-phenyl-4-propionyl-5-methylisoxazole prepared above in the procedure (2), 1.4 g (11.6 mmol) of piperidine hydrochloride, 0.4 g (13.3 mmol) of paraformaldehyde and 3 droplets of 12N-hydrochloric acid. The resultant mixture was heated under reflux for 30 minutes. After completion of the reaction, water and ethyl ether were added, followed by separation of a water layer. An aqueous solution of sodium carbonate was added to the water layer to alkalinize the same, followed by extraction with ethyl ether. The organic layer was dried and the solvent was distilled off, whereby a Mannich base, namely, 3-phenyl-5-methyl-4-(2-methyl-3-piperidinopropionyl)isoxazole was obtained as oil.

Workup

  1. temperatureunder reflux for 30 minutes
  2. additionwere added
  3. customfollowed by separation of a water layer
  4. additionAn aqueous solution of sodium carbonate was added to the water layer
  5. extractionfollowed by extraction with ethyl ether
  6. customThe organic layer was dried
  7. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-e67468f195f3461695ebdc356a3b03bb
Source dataset
uspto-grants-1996_03
Patent number
US05498619

Reaction notes

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