Potassium Carbonate → HCID 67746705, compound

HRID 866224Notes

Reaction equation

HRID 866224 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][C:5]2[C:6]([CH:9]3[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]3)=[N:7]O[C:4]=2[CH:3]=1.[C:17]([O-])([O-])=O.[K+].[K+].Br[CH2:24][CH2:25][C:26]#[N:27]>C(#N)C>[F:1][C:2]1[CH:16]=[CH:15][C:5]2[C:4]([CH:3]=1)=[CH:17][NH:7][C:6]=2[CH:9]1[CH2:14][CH2:13][N:12]([CH2:24][CH2:25][C:26]#[N:27])[CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 170203-BromopropionitrileHCID 8494213-(4-Piperidyl)-6-fluoro-1,2-benzisoxazole

Product 1

HCID 67746705HCID 67746705, compoundYield 31.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine (11 g, 50 mmol), K2CO3 (8.5 g, 74 mmol) and 3-bromopropionitrile (8.2 g, 1.2 eq) in acetonitrile (300 ml) was heated at reflux for 24 hours. The mixture was cooled and the insolubles were filtered. The solvent was removed on a rotary evaporator and the crude product was purified by flash chromatography over a silica gel column (SiO2, 120 g). The product thus purified weighed 8.94 g. Recrystallization from ethanol yielded the nitrile as white crystals 4.3 g, m.p. 100°-101° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 24 hours
  3. temperatureThe mixture was cooled
  4. filtrationthe insolubles were filtered
  5. customThe solvent was removed on a rotary evaporator
  6. customthe crude product was purified by flash chromatography over a silica gel column (SiO2, 120 g)
  7. customThe product thus purified
  8. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-2f258e39286d4dda92261a44ec1b8f01
Source dataset
uspto-grants-1996_10
Patent number
US05569653

Reaction notes

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