Hydrochloric Acid → 1-{2-{N-[4-(4-fluorophenyl)-4-oxobutyl]-N-methylamino}ethyl}-4-(4-trifluoromethyl-phenoxy)piperidine dihydrochloride

HRID 463316Notes

Reaction equation

HRID 463316 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][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:31][CH:30]=4)[CH2:24][CH2:23]3)[CH3:19])OCC[O:11]2)=[CH:6][CH:5]=1.Cl.C(=O)(O)[O-].[Na+]>CO>[ClH:1].[ClH:1].[F:3][C:4]1[CH:9]=[CH:8][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:30]=[CH:31][C:32]([C:35]([F:36])([F:37])[F:38])=[CH:33][CH:34]=3)[CH2:26][CH2:27]2)[CH3:19])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 20283118HCID 20283118, compound

Product 1

HCID 202830661-{2-{N-[4-(4-fluorophenyl)-4-oxobutyl]-N-methylamino}ethyl}-4-(4-trifluoromethyl-phenoxy)piperidine dihydrochlorideYield 101.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3.75 g (6.38 mmol) of 1-{2-{N-{3-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]propyl}-N-methylamino}ethyl}-4-(4-trifluoromethylphenoxy)piperidine dihydrochloride, 55 ml of methanol, and 22.5 ml of 3N HCl was heated at reflux under nitrogen for 3 hours. The reaction mixture was allowed to cool to room temperature and was subsequently neutralized with sodium bicarbonate. The methanol was evaporated and the residue made basic with sodium carbonate. The mixture was extracted with ether, washed with saturated sodium chloride and dried over potassium carbonate. Filtration followed by evaporation of the solvent provided an oil. The dihydrochloride was recrystallized from acetonitrile to provide 1.75 g (50%) of 1-{2-{N-[4-(4-fluorophenyl)-4-oxobutyl]-N-methylamino}ethyl}-4-(4-trifluoromethyl-phenoxy)piperidine dihydrochloride.

Workup

  1. temperatureat reflux under nitrogen for 3 hours
  2. customThe methanol was evaporated
  3. extractionThe mixture was extracted with ether
  4. washwashed with saturated sodium chloride
  5. dry with materialdried over potassium carbonate
  6. filtrationFiltration
  7. customfollowed by evaporation of the solvent
  8. customprovided an oil
  9. customThe dihydrochloride was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-1d447255fea3442db5613277fe232cfa
Source dataset
uspto-grants-1985_05
Patent number
US04518713

Reaction notes

Loading…