Pyrrolidine → HCID 19596453, compound

HRID 612929Notes

Reaction equation

HRID 612929 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.Br[CH2:7][CH2:8][O:9][C:10]1[CH:14]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[O:12][N:11]=1>>[C:15]1([C:13]2[O:12][N:11]=[C:10]([O:9][CH2:8][CH2:7][N:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)[CH:14]=2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 195964873-(2-Bromoethoxy)-5-phenylisoxazole

Product 1

HCID 19596453HCID 19596453, compoundYield 82%

Conditions

Temperature
100 °C

Procedure

Pyrrolidine (710 mg) was added to 3-(2-bromoethoxy)-5-phenylisoxazole (268 mg), and the mixture was stirred at 100° C. for one hour. After ice-cold water (20 ml) was added to the reaction mixture and the mixture was extracted with ether (20 ml×2), the organic layer was dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: ethyl acetate) to obtain the title compound (211 mg, 82%) as colorless crystals.

Workup

  1. extractionthe mixture was extracted with ether (20 ml×2)
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationAfter filtration
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: ethyl acetate)

Sources & evidence

ORD record
ord-b0703361af6d478d83baea8cdb18c74f
Source dataset
uspto-grants-1999_12
Patent number
US06005116

Reaction notes

Loading…