Potassium Carbonate → HCID 21960068, compound

HRID 233886Notes

Reaction equation

HRID 233886 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+].[CH3:23][O:24][CH2:25][CH2:26]Br.[C:28]([OH:35])(=[O:34])/[CH:29]=[CH:30]/[C:31]([OH:33])=[O:32]>C(#N)C.C(O)C>[C:28]([OH:35])(=[O:34])/[CH:29]=[CH:30]/[C:31]([OH:33])=[O:32].[CH3:23][O:24][CH2:25][CH2:26][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

7

Reactant 4

HCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 444972Fumaric AcidHCID 8494213-(4-Piperidyl)-6-fluoro-1,2-benzisoxazole

Product 1

HCID 21960068HCID 21960068, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 6342AcetonitrileSolvent

Procedure

A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (3.75 g, 17 mmol), K2CO3 (3 g, 21.7 mmol), bromoethyl methyl ether (2.84 g, 20.4 mmol) in acetonitrile (150 ml) was heated at reflux for 3.5 hours. The reaction was cooled. The inorganics were filtered and rinsed with DCM. The organic solution was concentrated down to an oil (7 g). Purification on a flash chromatography column (SiO2, 45 g; eluted with methanol/DCM) gave a light yellow oil as product (4 g, 87%). This oil was dissolved into ethanol and treated with a solution of fumaric acid (1.67 g) in ethanol (20 ml). White crystals (5.15 g) were collected, m.p.=157°-158° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3.5 hours
  3. temperatureThe reaction was cooled
  4. filtrationThe inorganics were filtered
  5. washrinsed with DCM
  6. concentrationThe organic solution was concentrated down to an oil (7 g)
  7. customPurification
  8. washon a flash chromatography column (SiO2, 45 g; eluted with methanol/DCM)
  9. customgave a light yellow oil as product (4 g, 87%)
  10. customWhite crystals (5.15 g) were collected

Sources & evidence

ORD record
ord-f9d6b0c80882491cbf08fa03604919e8
Source dataset
uspto-grants-1997_01
Patent number
US05593995

Reaction notes

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