Hydrochloric Acid → N-Benzyl-3-acetoxy-3-(m-trifluoromethylphenyl)piperidine hydrochloride

HRID 354837Notes

Reaction equation

HRID 354837 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][C:10]([OH:24])([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:25](OC(=O)C)(=[O:27])[CH3:26].S(=O)(=O)(O)O.[OH-].[Na+].[ClH:39]>C(O)C.C(OCC)(=O)C>[ClH:39].[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][C:10]([O:24][C:25](=[O:27])[CH3:26])([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:21])[F:22])[CH:15]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 205064151-Benzyl-3-(3-trifluoromethyl-phenyl)-piperidine-3-ol

Product 1

HCID 20506441N-Benzyl-3-acetoxy-3-(m-trifluoromethylphenyl)piperidine hydrochloride

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 37 g. of N-benzyl-3-hydroxy-3-(m-trifluoromethylphenyl)piperidine, 220 ml. of acetic anhydride and 0.3 ml. of concentrated sulfuric acid is heated to 110° C. for one hour. After cooling it is poured onto ice-water, the resulting mixture agitated for 15 minutes and made alkaline by addition of sodium hydroxide solution. The mixture is extracted with ethyl acetate, the extracts washed with brine, dried (MgSO4) and evaporated to dryness to obtain 39 g. of the free base. This is dissolved in 600 ml. of ethyl acetate, cooled in ice, and 100 ml. of ethanol saturated with hydrogen chloride is added. The solvent is removed by evaporation in vacuo and the residue triturated with 200 ml. of ethyl acetate then 200 ml. of ethyl ether is added and the mixture allowed to stand overnight. The crystalline title compounds is collected by filtration, washed with ether and dried to obtain 36 g., M.P. 206°-207° C.

Workup

  1. additionA mixture of 37 g
  2. temperatureAfter cooling it
  3. additionis poured onto ice-water
  4. extractionThe mixture is extracted with ethyl acetate
  5. washthe extracts washed with brine
  6. dry with materialdried (MgSO4)
  7. customevaporated to dryness
  8. customto obtain 39 g
  9. dissolutionThis is dissolved in 600 ml
  10. customThe solvent is removed by evaporation in vacuo
  11. customthe residue triturated with 200 ml
  12. additionof ethyl ether is added
  13. waitto stand overnight
  14. filtrationThe crystalline title compounds is collected by filtration
  15. washwashed with ether
  16. customdried
  17. customto obtain 36 g

Sources & evidence

ORD record
ord-fcbf3219e14d49d385eafc21373f5503
Source dataset
uspto-grants-1983_03
Patent number
US04377581

Reaction notes

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