3-(4-Piperidyl)-6-fluoro-1,2-benzisoxazole → HCID 15285671, compound

HRID 744316Notes

Reaction equation

HRID 744316 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.C1(C)C(S([C:26]2([C:37]3C=CC=C[CH:38]=3)[C:34](=[O:35])[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:27]2=[O:36])(=O)=O)=CC=CC=1>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]([CH2:38][CH2:37][C:26]4([C:2]5[CH:16]=[CH:15][CH:5]=[CH:4][CH:3]=5)[C:34](=[O:35])[C:33]5[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=5)[C:27]4=[O:36])[CH2:13][CH2:14]3)=[N:7][O:8][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 8494213-(4-Piperidyl)-6-fluoro-1,2-benzisoxazoleHCID 184673502-Toluenesulfonyl-2-phenyl-1,3-indandione

Product 1

HCID 15285671HCID 15285671, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine (2.2 g, 10 mmol), KCO3 (1.6 g, 11.6 mmol) and 2-toluenesulfonyl-2-phenyl-1,3-indandione (4.2 g, 10 mmol) in acetonitrile (50 ml) was heated at reflux for 3 hours. The mixture was cooled and the insolubles were filtered. The solvent was removed on a rotary evaporator. The residue was purified twice using a flash chromatography column (SiO2, 45 g and 40 g; eluted with DCM). The product thus purified was recrystallized from ethanol (30 ml) and isopropyl ether, yield: 2.8 g, m.p. 149°-150° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. temperatureThe mixture was cooled
  4. filtrationthe insolubles were filtered
  5. customThe solvent was removed on a rotary evaporator
  6. customThe residue was purified twice
  7. washa flash chromatography column (SiO2, 45 g and 40 g; eluted with DCM)
  8. customThe product thus purified
  9. customwas recrystallized from ethanol (30 ml) and isopropyl ether, yield: 2.8 g, m.p. 149°-150° C.

Sources & evidence

ORD record
ord-1867079ce9b14d2f80d98ecea0bd0c51
Source dataset
uspto-grants-1996_09
Patent number
US05559116

Reaction notes

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