Hydrochloric Acid → 3-{2-Methyl-3-(1-pyrrolidinyl)propionyl}-2,1-benzisoxazole hydrochloride

HRID 1440344Notes

Reaction equation

HRID 1440344 reaction equation
[C:1]([C:9]1[CH:13]=[C:12]([C:14](=[O:17])[CH2:15][CH3:16])[O:11][N:10]=1)(=O)[C:2]1[CH:7]=[CH:6]C=CC=1.C(C1O[N:24]=[C:25]2C=C[CH:28]=[CH:27][C:26]=12)(=O)CC.[ClH:31].N1CCC[CH2:33]1.C=O.Cl.Cl.O1CCOCC1>C(OCC)(=O)C.C(OCC)C.O.O1CCOCC1>[ClH:31].[CH3:33][CH:15]([CH2:16][N:24]1[CH2:25][CH2:26][CH2:27][CH2:28]1)[C:14]([C:12]1[O:11][N:10]=[C:9]2[CH:1]=[CH:2][CH:7]=[CH:6][C:13]=12)=[O:17]

Participants

11

Reactant 6

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 212848Pyrrolidine, hydrochloride (1:1)HCID 199769223-Propionyl-2,1-benzisoxazoleHCID 199769473-Benzoyl-5-propionylisoxazoleHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 199768993-{2-Methyl-3-(1-pyrrolidinyl)propionyl}-2,1-benzisoxazole hydrochloride

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

Added to 2 ml of dioxane were 2.0 g (11.4 mmol) of the ketone derivative, i.e., 3-propionyl-2,1-benzisoxazole prepared above in the procedure (2), 1.3 g (12.1 mmol) of pyrrolidine hydrochloride, 0.45 g (15.0 mmol) of paraformaldehyde and 2 droplets of 12N-hydrochloric acid. They were reacted under reflux for 30 minutes. After completion of the reaction, water and ethyl ether were added, and a water layer was collected. The water later was alkalinized with an aqueous solution of sodium carbonate and then extracted with ethyl ether. The extract was dried over anhydrous magnesium sulfate. The solvent was then distilled off so that an oily residue was obtained. The oily residue was dissolved in ethyl acetate, followed by the addition of a 4N-hydrochloric acid-dioxane solution under ice cooling. The mixture thus obtained was concentrated at room temperature under reduced pressure. Precipitated crystals of 3-{2-methyl-3-(1-pyrrolidinyl)propionyl}-2,1-benzisoxazole hydrochloride thus formed were collected by filtration, so that the title compound was obtained. Its yield was 0.9 g (30.5%).

Workup

  1. customThey were reacted
  2. temperatureunder reflux for 30 minutes
  3. additionwere added
  4. customa water layer was collected
  5. extractionextracted with ethyl ether
  6. dry with materialThe extract was dried over anhydrous magnesium sulfate
  7. distillationThe solvent was then distilled off so that an oily residue
  8. customwas obtained
  9. customThe mixture thus obtained
  10. concentrationwas concentrated at room temperature under reduced pressure
  11. customPrecipitated crystals of 3-{2-methyl-3-(1-pyrrolidinyl)propionyl}-2,1-benzisoxazole hydrochloride
  12. customthus formed
  13. filtrationwere collected by filtration, so that the title compound
  14. customwas obtained

Sources & evidence

ORD record
ord-7344a16ad1134f2aa615237fa96c5e11
Source dataset
uspto-grants-1996_03
Patent number
US05498619

Reaction notes

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