Hydrochloric Acid → 1-[3-(6-Fluoro-1,2-benzisoxazol-3-yl)propyl]-4-piperidone

HRID 280892Notes

Reaction equation

HRID 280892 reaction equation
Cl.[F:2][C:3]1[CH:24]=[CH:23][C:6]2[C:7]([CH2:10][CH2:11][CH2:12][N:13]3[CH2:22][CH2:21][C:16]4(OCC[O:17]4)[CH2:15][CH2:14]3)=[N:8][O:9][C:5]=2[CH:4]=1.O.Cl.[OH-].[Na+]>C(O)C>[F:2][C:3]1[CH:24]=[CH:23][C:6]2[C:7]([CH2:10][CH2:11][CH2:12][N:13]3[CH2:14][CH2:15][C:16](=[O:17])[CH2:21][CH2:22]3)=[N:8][O:9][C:5]=2[CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 233157868-[3-(6-Fluoro-1,2-benzisoxazol-3-yl)propyl]-1,4-dioxa-8-azaspiro[4.5]decane hydrochloride

Product 1

HCID 132078191-[3-(6-Fluoro-1,2-benzisoxazol-3-yl)propyl]-4-piperidoneYield 96%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 51 g of 8-[3-(6-fluoro-1,2-benzisoxazol-3-yl)propyl]-1,4-dioxa-8-azaspiro[4.5]decane hydrochloride, 100 ml of water, 100 ml of ethanol and 150 ml of 3N hydrochloric acid was heated at 75°-80° C. for 3 hrs and at ambient temperature overnight, with stirring. The mixture was cooled, basified with 3N sodium hydroxide solution and extracted with ethyl acetate-ether. The organic extracts were washed with water, saturated sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated to give 37 g (96%) of product as an oil.

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with ethyl acetate-ether
  3. washThe organic extracts were washed with water, saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e37339c596cd4237bf0e043d0cbfdef0
Source dataset
uspto-grants-1986_05
Patent number
US04591586

Reaction notes

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