Potassium Carbonate → 3-Methoxybenzamide

HRID 1069282Notes

Reaction equation

HRID 1069282 reaction equation
FC1C=CC2C(C3CCNCC3)=NOC=2C=1.C([O-])([O-])=O.[K+].[K+].BrCCCO[C:28]1[CH:36]=[CH:35][C:31]([C:32]([NH2:34])=[O:33])=[CH:30][C:29]=1[O:37][CH3:38]>C(#N)C>[CH3:38][O:37][C:29]1[CH:30]=[C:31]([CH:35]=[CH:36][CH:28]=1)[C:32]([NH2:34])=[O:33]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 8494213-(4-Piperidyl)-6-fluoro-1,2-benzisoxazoleHCID 101081354-(3-Bromopropoxy)3-methoxybenzamide

Product 1

HCID 984873-Methoxybenzamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (2.2 g, 10.0 mmol), K2CO3 (2.0 g) and 4-(3bromopropoxy)-3-methoxybenzamide (2.32 g, 8.0 mmol) in acetonitrile (80 ml) was heated at reflux for 5 hours. At the end of the reaction the solvent was evaporated. The residue was extracted into dichloromethane. The inorganic insolubles were filtered off. The dichloromethane was concentrated again. The crude residue was purified by flash chromatography over a silica gel column (55 g, SiO2; eluted with 1% methanol in dichloromethane, 1 l; 2% methanol in dichloromethane, 1 l). The material thus obtained weighed 2.93 g (84%) as white crystals. Recrystallization from hot ethanol (60 ml) gave 2.2 g of 4-[3-4(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]propoxy]-3-methoxybenzamide as white crystals, m.p.=163-164° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 5 hours
  3. customAt the end of the reaction the solvent
  4. customwas evaporated
  5. extractionThe residue was extracted into dichloromethane
  6. filtrationThe inorganic insolubles were filtered off
  7. concentrationThe dichloromethane was concentrated again
  8. customThe crude residue was purified by flash chromatography over a silica gel column (55 g, SiO2; eluted with 1% methanol in dichloromethane, 1 l; 2% methanol in dichloromethane, 1 l)
  9. customThe material thus obtained
  10. customRecrystallization from hot ethanol (60 ml)

Sources & evidence

ORD record
ord-09290611e2264a9f876fe2e4a23d33b8
Source dataset
uspto-grants-2001_06
Patent number
US06251907B1

Reaction notes

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