Acetonitrile → 2-[4-(6-Fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl acetate fumarate

HRID 2184544Notes

Reaction equation

HRID 2184544 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([O-])([O-])=O.[K+].[K+].[C:23]([OH:30])(=[O:29])/[CH:24]=[CH:25]/[C:26]([OH:28])=[O:27].[C:31](#N)[CH3:32]>C(O)C>[C:23]([OH:30])(=[O:29])/[CH:24]=[CH:25]/[C:26]([OH:28])=[O:27].[C:26]([O:28][CH2:31][CH2:32][N:12]1[CH2:11][CH2:10][CH:9]([C:6]2[C:5]3[CH:15]=[CH:16][C:2]([F:1])=[CH:3][C:4]=3[O:8][N:7]=2)[CH2:14][CH2:13]1)(=[O:27])[CH3:25]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 444972Fumaric AcidHCID 8494213-(4-Piperidyl)-6-fluoro-1,2-benzisoxazole

Product 1

HCID 219600152-[4-(6-Fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl acetate fumarate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (3.0 g, 13.6 mmol), K2CO3 (3.5 g, 25 mmol) 2-bromoethyl acetate (4 g, 26.5 mmol) in acetonitrile (50 ml) was heated at reflux for 4 hours. After cooling to room temperature, the inorganic salts were filtered and washed with DCM (dichloromethane 50 ml). The organic solvent was removed on a rotary evaporator to give an oil. The oily product was purified on a flash chromatography column (60 g of SiO2; eluted with MeOH 2%-4% in DCM). The pure product thus obtained weighed 4.43 g. This oil was dissolved in ethanol and treated with a solution of fumaric acid (1.2 g) in ethanol. The sale crystallized out at room temperature to yield 3.44 g (57%) m.p.=154°-155° C. ANALYSIS: Calculated for C10H19FN2O3.C4H4O4: 56.86%C 5.49%H 6.63%N Found: 56.75%C 5.41%H 6.54%N

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours
  3. filtrationthe inorganic salts were filtered
  4. washwashed with DCM (dichloromethane 50 ml)
  5. customThe organic solvent was removed on a rotary evaporator
  6. customto give an oil
  7. customThe oily product was purified on a flash chromatography column (60 g of SiO2; eluted with MeOH 2%-4% in DCM)
  8. customThe pure product thus obtained
  9. customThe sale crystallized out at room temperature
  10. customto yield 3.44 g (57%) m.p.=154°-155° C

Sources & evidence

ORD record
ord-318db4614e1a4690b29c107c16293e91
Source dataset
uspto-grants-2002_06
Patent number
USRE037729E1

Reaction notes

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