Potassium Carbonate → HCID 21960051, compound

HRID 2184503Notes

Reaction equation

HRID 2184503 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:23][C:24]1[CH:25]=[C:26]([C:35](=[O:37])[CH3:36])[CH:27]=[CH:28][C:29]=1[O:30][CH2:31][CH2:32][CH2:33]Br>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]([CH2:33][CH2:32][CH2:31][O:30][C:29]4[CH:28]=[CH:27][C:26]([C:35](=[O:37])[CH3:36])=[CH:25][C:24]=4[Br:23])[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 21960047HCID 21960047, compound

Product 1

HCID 21960051HCID 21960051, compoundYield 68.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (2.1 g, 9.5 mmol ). K2CO3 (2.0 g)-1-[3-bromo-4-(3-bromopropoxy)phenyl]ethanone (3.1 g, 9.2 mmol) in acetonitrile (100 ml) was heated at reflux for 3 hours. At the end of reaction, the solvent was concentrated and the mixture was extracted into dichloromethane (200 ml). The insolubles were filtered off. The dichloromethane was concentrated again. The crude residue was purified by flash chromatography over a silica gel column. (SiO2, 49 g; eluted with dichloromethane, 500 ml; 1% methanol:dichloromethane, 600 ml; 3% methanol; 97% dichloromethane, 600 ml). The material thus obtained (3.26 g, 72%) was recrystallized from ethanol (40 ml) to give 1-[4-[3-[4-(6-fluoro-1,2-benzisoxazol -3- yl)-1-piperidinyl]-propoxy]-3-bromophenyl]ethanone as light yellow crystals (3.0 g), m.p.=126°-128° C. ANALYSIS: Calculated for C23H24BrFN2O3: 58.12%C 5.09%H 5.89%N Found: 57.64%C 5.35%H 5.55%N

Workup

  1. temperatureat reflux for 3 hours
  2. customAt the end of reaction
  3. concentrationthe solvent was concentrated
  4. extractionthe mixture was extracted into dichloromethane (200 ml)
  5. filtrationThe insolubles were filtered off
  6. concentrationThe dichloromethane was concentrated again
  7. customThe crude residue was purified by flash chromatography over a silica gel column
  8. wash(SiO2, 49 g; eluted with dichloromethane, 500 ml; 1% methanol:dichloromethane, 600 ml; 3% methanol; 97% dichloromethane, 600 ml)
  9. customThe material thus obtained (3.26 g, 72%)
  10. customwas recrystallized from ethanol (40 ml)

Sources & evidence

ORD record
ord-00f67b037b8b4879a41ce9d4194f404e
Source dataset
uspto-grants-2002_06
Patent number
USRE037729E1

Reaction notes

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