Pyrrolidine → HCID 19976914, compound

HRID 1440339Notes

Reaction equation

HRID 1440339 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:6]1([C:12]2[CH:16]=[C:15]([C:17]([C:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH:20]=3)=[O:18])[O:14][N:13]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>>[C:6]1([C:12]2[CH:16]=[C:15]([C:17]([CH:19]3[CH2:20][CH2:21][CH2:22][CH2:23][CH:24]3[N:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[O:18])[O:14][N:13]=2)[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 19976965HCID 19976965, compound

Product 1

HCID 19976914HCID 19976914, compound

Procedure

Pyrrolidine (5 ml) was added to 0.98 g (3.9 mmol) of 3-phenyl-5-(1-cyclohexenoyl)isoxazole prepared above in the procedure (1). The resultant mixture was stirred at room temperature for 1 hour and then concentrated under reduced pressure. To the concentrate was added diethyl ether and then 10% hydrochloric acid, whereby the reaction product was extracted in a water layer. The water layer was collected, alkalinized with a 10% aqueous solution of sodium hydroxide, and then extracted with dichloromethane. The solvent was distilled off, so that 3-phenyl- 5-{2-(1-pyrrolidinyl)cyclohexanoyl}isoxazole was obtained as yellow crystals.

Workup

  1. customprepared above in the procedure (1)
  2. concentrationconcentrated under reduced pressure
  3. additionTo the concentrate was added diethyl ether
  4. extraction10% hydrochloric acid, whereby the reaction product was extracted in a water layer
  5. customThe water layer was collected
  6. extractionextracted with dichloromethane
  7. distillationThe solvent was distilled off, so that 3-phenyl- 5-{2-(1-pyrrolidinyl)cyclohexanoyl}isoxazole
  8. customwas obtained as yellow crystals

Sources & evidence

ORD record
ord-deb5b8add8fd492f801d6212c5e83bc3
Source dataset
uspto-grants-1996_03
Patent number
US05498619

Reaction notes

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