Hydrochloric Acid → 1-{2-{-N-[4-(4-Fluorophenyl)-4-oxobutyl]-N-methylamino}ethyl}-4-(3-chlorophenoxy)piperidine dihydrochloride

HRID 463308Notes

Reaction equation

HRID 463308 reaction equation
[ClH:1].Cl.[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2([CH2:15][CH2:16][CH2:17][N:18]([CH2:20][CH2:21][N:22]3[CH2:27][CH2:26][CH:25]([O:28][C:29]4[CH:34]=[CH:33][CH:32]=[C:31]([Cl:35])[CH:30]=4)[CH2:24][CH2:23]3)[CH3:19])OCC[O:11]2)=[CH:6][CH:5]=1.Cl.C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl>CO>[ClH:35].[ClH:1].[F:3][C:4]1[CH:5]=[CH:6][C:7]([C:10](=[O:11])[CH2:15][CH2:16][CH2:17][N:18]([CH2:20][CH2:21][N:22]2[CH2:23][CH2:24][CH:25]([O:28][C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([Cl:35])[CH:30]=3)[CH2:26][CH2:27]2)[CH3:19])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 202830781-{2-{N-{3-[2-(4-Fluorophenyl)-1,3-dioxolan-2-yl]-propyl}-N-methylamino}ethyl}-4-(3-chlorophenoxy)piperidine dihydrochloride

Product 1

HCID 202830441-{2-{-N-[4-(4-Fluorophenyl)-4-oxobutyl]-N-methylamino}ethyl}-4-(3-chlorophenoxy)piperidine dihydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution prepared from 8.55 g (15.5 mmol) of 1-{2-{N-{3-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]propyl}-N-methylamino}ethyl}-4-(3-chlorophenoxy)piperidine dihydrochloride, 130 ml of methanol and 50 ml of 3N HCl was heated at reflux for 3 hours under nitrogen and allowed to cool to room temperature. The methanol was evaporated and the residue made basic with saturated sodium carbonate and extracted with ether. The ether extract was washed with saturated sodium chloride and dried over potassium carbonate. Filtration followed by evaporation of the solvent provided an oil. The yield of the dihydrochloride was 6.8 g (13.4 mmol, 86%). Recrystallization from ethanol/methanol provided analytically pure material.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours under nitrogen
  3. customThe methanol was evaporated
  4. extractionextracted with ether
  5. extractionThe ether extract
  6. washwas washed with saturated sodium chloride
  7. dry with materialdried over potassium carbonate
  8. filtrationFiltration
  9. customfollowed by evaporation of the solvent
  10. customprovided an oil
  11. customRecrystallization from ethanol/methanol
  12. customprovided analytically pure material

Sources & evidence

ORD record
ord-8e6ea5049fa748f1adbf86de1906491d
Source dataset
uspto-grants-1985_05
Patent number
US04518713

Reaction notes

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