Hydrochloric Acid → 6-Fluoro-3-(4-piperidinyl)-1,2-benzisothiazole

HRID 1246560Notes

Reaction equation

HRID 1246560 reaction equation
[F:1][C:2]1[CH:18]=[CH:17][C:5]2[C:6]([CH:9]3[CH2:14][CH2:13][N:12](C=O)[CH2:11][CH2:10]3)=[N:7][S:8][C:4]=2[CH:3]=1.Cl.C(O)C.[OH-].[Na+]>O>[F:1][C:2]1[CH:18]=[CH:17][C:5]2[C:6]([CH:9]3[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]3)=[N:7][S:8][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 21915434HCID 21915434, compound

Product 1

HCID 185049766-Fluoro-3-(4-piperidinyl)-1,2-benzisothiazoleYield 86.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Reflux a solution of 4-(6-fluoro-1,2-benzisothiazol-3-yl)-1-piperidinecarboxaldehyde (Tetrahedron Lett., 1993, 34, 6525–6528, 12 g, 0.045 mol), 3N hydrochloric acid and ethanol (100 mL) for 3 hours. Stir at ambient temperature for 16 hours, add water and stir with ice bath chilling while adding sodium hydroxide solution until the mixture was basic. Extract with ethyl acetate, wash the extract with water, dry (MgSO4), filter and concentrate the filtrate to afford an oil which solidified on standing to afford 6-fluoro-3-(4-piperidinyl)-1,2-benzisothiazole (9.2 g). React 6-fluoro-3-(4-piperidinyl)-1,2-benzisothiazole under conditions as described for Example 11 to afford the title compound (0.25 g, 61% yield), LC/MS (APCI) m/e 510 (MH+), retention time 4.38 min.

Workup

  1. stirringstir with ice bath
  2. temperaturechilling
  3. extractionExtract with ethyl acetate
  4. washwash the
  5. extractionextract with water
  6. dry with materialdry (MgSO4)
  7. filtrationfilter
  8. concentrationconcentrate the filtrate
  9. customto afford an oil which

Sources & evidence

ORD record
ord-94630315542c41cf9bebe7d78fde8120
Source dataset
uspto-grants-2006_10
Patent number
US07125903B1

Reaction notes

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