Potassium Carbonate → HCID 21960114, compound

HRID 581543Notes

Reaction equation

HRID 581543 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:17]([O-:20])([O-:19])=O.[K+].[K+].Br[CH2:24][CH2:25][CH:26]1[O:31][CH2:30][CH2:29][CH2:28][O:27]1>C(#N)C>[C:26]([OH:31])(=[O:27])/[CH:25]=[CH:24]/[C:17]([OH:20])=[O:19].[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][CH:26]4[O:31][CH2:30][CH2:29][CH2:28][O:27]4)[CH2:13][CH2:14]3)=[N:7][O:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5206561,3-Dioxane, 2-(2-bromoethyl)-HCID 8494213-(4-Piperidyl)-6-fluoro-1,2-benzisoxazole

Product 1

HCID 21960114HCID 21960114, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (2.0 g, 9.1 mmol), K2CO3 (1.5 g, 10.9 mmol) and bromoethyl-1,3-dioxane (2.1 g, 10.7 mmol) in acetonitrile (50 ml) was heated at reflux for 3 hours. At the end, the insolubles were filtered and rinsed with DCM and the filtrate was evaporated down. The crude mixture was purified by flash chromatography over a silica gel column (Sorbsil C-30, 25 g; eluted with DCM and MEOH (1-3%) in DCM). The fractions containing the pure product with DCM and MEOH (1-3%) in DCM). The fractions containing the pure product fumaric acid (1.0 g) ethanol solution. The crystals were collected: 3.98 g (77%), m.p.=161-162° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. filtrationAt the end, the insolubles were filtered
  4. washrinsed with DCM
  5. customthe filtrate was evaporated down
  6. customThe crude mixture was purified by flash chromatography over a silica gel column (Sorbsil C-30, 25 g; eluted with DCM and MEOH (1-3%) in DCM)
  7. additionThe fractions containing the pure product with DCM and MEOH (1-3%) in DCM)
  8. additionThe fractions containing the pure product fumaric acid (1.0 g) ethanol solution
  9. customThe crystals were collected

Sources & evidence

ORD record
ord-f43dbaf837254bfa89e2d9295f12bac2
Source dataset
uspto-grants-1999_07
Patent number
US05919798

Reaction notes

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