3-(4-Piperidyl)-6-fluoro-1,2-benzisoxazole → HCID 15816944, compound

HRID 1456742Notes

Reaction equation

HRID 1456742 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.BrCCCC[C:22]1[CH:32]=[CH:31][CH:30]=[C:24]2[C:25]([NH:27][C:28](=[O:29])[C:23]=12)=[O:26]>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]([CH2:16][CH2:2][CH2:3][CH2:4][N:27]4[C:28](=[O:29])[C:23]5=[CH:22][CH:32]=[CH:31][CH:30]=[C:24]5[C:25]4=[O:26])[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 21960043Bromobutylphthalimide

Product 1

HCID 15816944HCID 15816944, compoundYield 47.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 6 -fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (5.5 g, 25 mmol), 4-bromobutylphthalimide (8.0 g, 28.3 mmol, 1.13 eq), K2 CO3 (4.55 g, 32 mmol) in acetonitrile (100 ml) was heated at reflux for 3 hours. At the end of the reaction, the mixture was filtered. The insolubles were washed with dichloromethane (200 ml). The organic solution was concentrated gradually to allow cystallization. The crude crystals (5.9 g) were collected. The mother liquor was concentrated to a solid (5.5 g,). Purification was by flash chromatography over a silica gel column. The product (3.8 g) thus purified was recrystallized from ethanol (70 ml) to give 2.48 g of N-[4-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]butyl]phthalimide as white crystals, m.p.=144°-146° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. customAt the end of the reaction
  4. filtrationthe mixture was filtered
  5. washThe insolubles were washed with dichloromethane (200 ml)
  6. concentrationThe organic solution was concentrated gradually
  7. customThe crude crystals (5.9 g) were collected
  8. concentrationThe mother liquor was concentrated to a solid (5.5 g,)
  9. customPurification
  10. customThe product (3.8 g) thus purified
  11. customwas recrystallized from ethanol (70 ml)

Sources & evidence

ORD record
ord-410f199545084a828025da6b4e5eb283
Source dataset
uspto-grants-1998_12
Patent number
US05843977

Reaction notes

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