Acetonitrile → HCID 67070941, compound

HRID 1955884Notes

Reaction equation

HRID 1955884 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][C:5]2[C:6]([CH:9]3[CH2:14][CH2:13]NCC3)=[N:7][O:8][C:4]=2[CH:3]=1.C([O-])([O-])=O.[K+].[K+].BrCCC[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[O:34][CH3:35].[C:36]([OH:43])(=[O:42])/[CH:37]=[CH:38]\[C:39]([OH:41])=[O:40].[C:44](#[N:46])[CH3:45]>C(O)C>[C:36]([OH:43])(=[O:42])/[CH:37]=[CH:38]\[C:39]([OH:41])=[O:40].[F:1][C:2]1[CH:16]=[CH:15][C:5]2[C:6]([CH2:9][CH2:14][CH2:13][CH:27]([N:46]3[CH2:38][CH2:37][CH2:36][CH2:45][CH2:44]3)[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[O:34][CH3:35])=[N:7][O:8][C:4]=2[CH:3]=1

Participants

7

Reactant 5

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 444266Maleic AcidHCID 8494213-(4-Piperidyl)-6-fluoro-1,2-benzisoxazoleHCID 190724681-(4-Bromobutyl)-2-methoxybenzene

Product 1

HCID 67070941HCID 67070941, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (2.36 g, 10.7 mmole), K2CO3 (2 g, 14.5 mmol) and 2-(4-bromobutyl)anisole (2.4 g, 10 mmol) in acetonitrile (100 mnl) was heated at reflux for 2.5 hours. At the end of reaction, the solvent was removed. The residue was extracted into dichloromethane (200 ml) and filtered. The dichloromethane solution was concentrated. The crude oil obtained was purified on a flash chromatography column. The material thus purified was a light yellow oil (2.73 g, 53%). This oil was dissolved in ethanol and treated with maleic acid (607 mg, 1.0 eq) in ethanol. The 4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-(2'-methoxyphenyl)- butylpiperidine maleate crystals formed on concentration and subsequent cooling to O0 °C. These were collected and dried to yield 2.05 g, m.p.=132°-133°C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2.5 hours
  3. customAt the end of reaction
  4. customthe solvent was removed
  5. extractionThe residue was extracted into dichloromethane (200 ml)
  6. filtrationfiltered
  7. concentrationThe dichloromethane solution was concentrated
  8. customThe crude oil obtained
  9. customwas purified on a flash chromatography column
  10. customThe material thus purified
  11. dissolutionThis oil was dissolved in ethanol

Sources & evidence

ORD record
ord-c14698a92a0f49ccb314b3a22a11fc91
Source dataset
uspto-grants-1998_07
Patent number
US05776963

Reaction notes

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