Potassium Carbonate → HCID 10386866, compound

HRID 1069271Notes

Reaction equation

HRID 1069271 reaction equation
Cl.[F:2][C:3]1[CH:17]=[CH:16][C:6]2[C:7]([CH:10]3[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]3)=[N:8][O:9][C:5]=2[CH:4]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:25][CH2:26][CH2:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([C:35](=[O:37])[CH3:36])=[C:31]([CH3:38])[CH:30]=1>CN(C)C=O.C(#N)C>[F:2][C:3]1[CH:17]=[CH:16][C:6]2[C:7]([CH:10]3[CH2:11][CH2:12][N:13]([CH2:25][CH2:26][CH2:27][O:28][C:29]4[CH:34]=[CH:33][C:32]([C:35](=[O:37])[CH3:36])=[C:31]([CH3:38])[CH:30]=4)[CH2:14][CH2:15]3)=[N:8][O:9][C:5]=2[CH:4]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11334359R-56109 hydrochlorideHCID 11777949HCID 11777949, compound

Product 1

HCID 10386866HCID 10386866, compoundYield 3,982.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
120 °C

Procedure

A stirred mixture of 6-fluoro-3-(4-piperidinyl)-1,2 benzisoxazole hydrochloride (5.5 g 21.6 mmol), K2CO3(3.5 g), 1-[4-(3bromopropoxy)-2-methylphenyl]-ethanone (4.83 g, 17.8 mmol) in dimethylformamide (25 ml) and acetonitrile (75 ml) was heated at 120° C. for 5 hours. At the end of the reaction, the solvent was removed and the residue was extracted into dichloromethane (300 ml) and the solution was washed with water and brine. The organic solution was dried and evaporated to a crude oil. The purification was done by flash chromatography over a silica gel column (80 g, eluted with dichloromethane, 1 l; 1% methanol: dichloromethane, 1.2 l; 2% methanol dichloromethane, 1.2 l). The purest fractions were combined and afforded 291 g of solid. Recrystallization from dichloromethane and ethanol gave 1-[4-[3-4-(6fluoro-1,2-benzisoxazol-3yl)-1-piperidinyl]propoxy]-2-methylphenyl]ethanone as off-white crystals: 2.42 g, m.p.=113-114° C.

Workup

  1. customAt the end of the reaction
  2. customthe solvent was removed
  3. extractionthe residue was extracted into dichloromethane (300 ml)
  4. washthe solution was washed with water and brine
  5. customThe organic solution was dried
  6. customevaporated to a crude oil
  7. customThe purification
  8. washwas done by flash chromatography over a silica gel column (80 g, eluted with dichloromethane, 1 l; 1% methanol: dichloromethane, 1.2 l; 2% methanol dichloromethane, 1.2 l)

Sources & evidence

ORD record
ord-be5aa7b71309439ebdb57b987d881439
Source dataset
uspto-grants-2001_06
Patent number
US06251907B1

Reaction notes

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