Potassium Carbonate → HCID 86752898, compound

HRID 1955851Notes

Reaction equation

HRID 1955851 reaction equation
FC1C=CC2C(C3CCNCC3)=NOC=2C=1.C([O-])([O-])=O.[K+].[K+].BrCCCO[C:28]1[CH:33]=[CH:32][C:31]([C:34](=[O:36])[CH3:35])=[CH:30][CH:29]=1.[F:37][C:38]1[CH:65]=[CH:64][C:41]2[C:42]([CH:45]3[CH2:50][CH2:49][N:48]([CH2:51][CH2:52][CH2:53][O:54]C4C=CC(C(=O)C)=CC=4)[CH2:47][CH2:46]3)=[N:43][O:44][C:40]=2[CH:39]=1>C(#N)C>[F:37][C:38]1[CH:65]=[CH:64][C:41]2[C:42]([CH:45]3[CH2:50][CH2:49][N:48]([CH2:51][CH2:52][C:53]([C:28]4[CH:29]=[CH:30][C:31]([C:34](=[O:36])[CH3:35])=[CH:32][CH:33]=4)=[O:54])[CH2:47][CH2:46]3)=[N:43][O:44][C:40]=2[CH:39]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 8494213-(4-Piperidyl)-6-fluoro-1,2-benzisoxazoleHCID 10061000HCID 10061000, compoundHCID 10453356HCID 10453356, compound

Product 1

HCID 86752898HCID 86752898, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 6fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (3.27 & 14.8 mmol), K2CO3 (3 g), 1-[4-(3-bromopropoxy)phenyl]ethanone (4.5 g, 17.5 mmol) in acetonitrile (60 ml) was heated at reflux for 4 hours. 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, 1 liter). The purest fractions were combined and gave 2.8 g, 48%, of 1-[4-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]propoxy]phenyl]ethanone, m.p.=111-112° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours
  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, 1 liter)
  8. customgave 2.8 g, 48%

Sources & evidence

ORD record
ord-66055026e93049dba65b1730faeda416
Source dataset
uspto-grants-1998_07
Patent number
US05776963

Reaction notes

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