Potassium Carbonate → HCID 10453356, compound

HRID 1792653Notes

Reaction equation

HRID 1792653 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[CH:33]=[CH:32][C:31]([C:34](=[O:36])[CH3:35])=[CH:30][CH:29]=1>C(#N)C>[F:1][C:2]1[CH:16]=[CH:15][C:5]2[C:6]([CH:9]3[CH2:10][CH2:11][N:12]([CH2:24][CH2:25][CH2:26][O:27][C:28]4[CH:33]=[CH:32][C:31]([C:34](=[O:36])[CH3:35])=[CH:30][CH:29]=4)[CH2:13][CH2:14]3)=[N:7][O:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 8494213-(4-Piperidyl)-6-fluoro-1,2-benzisoxazoleHCID 10061000HCID 10061000, compound

Product 1

HCID 10453356HCID 10453356, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (3.27 g, 14.8 mmoles), K2CO3(3 g), 1-[4-(3-bromopropoxy)phenyl]ethanone (4.5 g, 17.5 mmoles) in acetonitrile (60 ml) was heated at reflux for 4 hr. The solvent was removed. The residue was dissolved in dichloromethane (300 ml) and washed with water and brine, then dried over MgSO4. The crude product from the evaporated solution was purified by flash chromatography (SiO2. 60 g; eluted with 1% methanol in dichloromethane, methane 1liter). The purest fractions were combined and gave 2.8 g, 48% of 1-[4-[3-[4-(6-fluoro-1,2benzisoxazol-3-yl)-1-piperidinyl]propoxy)phenyl]ethanone, m.p.=111°-112° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 hr
  3. customThe solvent was removed
  4. dissolutionThe residue was dissolved in dichloromethane (300 ml)
  5. washwashed with water and brine
  6. dry with materialdried over MgSO4
  7. customThe crude product from the evaporated solution was purified by flash chromatography (SiO2. 60 g; eluted with 1% methanol in dichloromethane, methane 1liter)

Sources & evidence

ORD record
ord-1a145ba0c2bc4bd290e7eaba5b81f228
Source dataset
uspto-grants-2006_07
Patent number
USRE039198E1

Reaction notes

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