Potassium Carbonate → 1-[3,5-Dibromo-4-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]propoxy]phenyl]ethanone

HRID 1955854Notes

Reaction equation

HRID 1955854 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:8][C:4]=2[CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:24][CH2:25][CH2:26][O:27][C:28]1[C:33]([Br:34])=[CH:32][C:31]([C:35](=[O:37])[CH3:36])=[CH:30][C:29]=1[Br:38]>C(#N)C>[Br:34][C:33]1[CH:32]=[C:31]([C:35](=[O:37])[CH3:36])[CH:30]=[C:29]([Br:38])[C:28]=1[O:27][CH2:26][CH2:25][CH2:24][N:12]1[CH2:11][CH2:10][CH:9]([C:6]2[C:5]3[CH:15]=[CH:16][C:2]([F:1])=[CH:3][C:4]=3[O:8][N:7]=2)[CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 8494213-(4-Piperidyl)-6-fluoro-1,2-benzisoxazoleHCID 219601181-[4-(3-Bromopropoxy)-3,5-dibromophenyl]ethanone

Product 1

HCID 219600591-[3,5-Dibromo-4-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]propoxy]phenyl]ethanone

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A stirred midxture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (2.0 g, 9.0 mmol), K2CO3 (1.3 g), and 1-[4-(3-bromopropoxy)-3,5-dibromophenyl]ethanon (2.65 g, 9.0 mmol) and acetonitrile (50 ml) was heated at reflux for 3 hours. At the end of the reaction, the solvent was evaporated and the residue was extracted into dichoromethane (150 ml). The insolubles were filtered off. The dichloromethane solution was concentrated down to an oil. The purification was done by flash chromatography on a silica gel column (SiO2, 47 g; eluted with dichioromethane, 2 co300 ml; 1% methanol n dichloromethane, 600 ml). Th e material thus purified as a colorless off, solidified on standing. RecrystalAtion from ethanol gave 1-[3,5-dibromo-4-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-l-piperidinyl]propoxyl]-phenyl]ethanone as white crystals (2.93 g 57%), m.p .=102-103° C.

Workup

  1. temperatureat reflux for 3 hours
  2. customAt the end of the reaction
  3. customthe solvent was evaporated
  4. extractionthe residue was extracted into dichoromethane (150 ml)
  5. filtrationThe insolubles were filtered off
  6. concentrationThe dichloromethane solution was concentrated down to an oil
  7. customThe purification
  8. washwas done by flash chromatography on a silica gel column (SiO2, 47 g; eluted with dichioromethane, 2 co300 ml; 1% methanol n dichloromethane, 600 ml)
  9. customTh e material thus purified as a colorless off,

Sources & evidence

ORD record
ord-7f9b402dc7ce4025ae4cbc23b235d4d9
Source dataset
uspto-grants-1998_07
Patent number
US05776963

Reaction notes

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