Hydrochloric Acid → HCID 131719829, compound

HRID 363625Notes

Reaction equation

HRID 363625 reaction equation
C([O:4][CH2:5][CH2:6][N:7]1[CH2:12][CH2:11][CH:10]([C:13]2[C:17]3[CH:18]=[CH:19][C:20]([F:22])=[CH:21][C:16]=3[O:15][N:14]=2)[CH2:9][CH2:8]1)(=O)C.[OH-].[Na+].Cl.[C:26]([OH:33])(=[O:32])/[CH:27]=[CH:28]/[C:29]([OH:31])=[O:30]>C(O)C>[C:26]([OH:33])(=[O:32])/[CH:27]=[CH:28]/[C:29]([OH:31])=[O:30].[F:22][C:20]1[CH:19]=[CH:18][C:17]2[C:13]([CH:10]3[CH2:11][CH2:12][N:7]([CH2:6][CH2:5][OH:4])[CH2:8][CH2:9]3)=[N:14][O:15][C:16]=2[CH:21]=1.[F:22][C:20]1[CH:19]=[CH:18][C:17]2[C:13]([CH:10]3[CH2:11][CH2:12][N:7]([CH2:6][CH2:5][OH:4])[CH2:8][CH2:9]3)=[N:14][O:15][C:16]=2[CH:21]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 444972Fumaric AcidHCID 21960016HCID 21960016, compound

Product 1

HCID 131719829HCID 131719829, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

2-[4-(6-Fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl acetate (10.58 g, 34.6 mmol), 15% NaOH (100 ml) and ethanol (100 ml) was heated at reflux for 4 hours. The solution was cooled (~5° C.) and neutralized with HCl to pH~7. The ethanol was removed under reduced pressure. The aqueous solution was basified with NaHCO3 and extracted with DCM (2×200 ml). The DCM solution was washed with brine and dried over MgSO4 and evaporated to give a white solid: 6.88 g (75%). A sample (2.03 g) was dissolved in ethanol and treated with fumaric acid (660 mg, 1.0 eq). Crystallization was induced with drops of isopropyl ether to yield off-white crystals: 1.43 g, m.p.=159°-161° C.

Workup

  1. temperatureat reflux for 4 hours
  2. temperatureThe solution was cooled (~5° C.)
  3. customThe ethanol was removed under reduced pressure
  4. extractionextracted with DCM (2×200 ml)
  5. washThe DCM solution was washed with brine
  6. dry with materialdried over MgSO4
  7. customevaporated
  8. customto give a white solid
  9. customCrystallization
  10. customto yield off-white crystals

Sources & evidence

ORD record
ord-d8495a9128c14a78ab2eb69fda912124
Source dataset
uspto-grants-1999_02
Patent number
US05874435

Reaction notes

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