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

HRID 463315Notes

Reaction equation

HRID 463315 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][CH2:22][N:23]3[CH2:28][CH2:27][CH:26]([O:29][C:30]4[CH:35]=[CH:34][CH:33]=[C:32]([Cl:36])[CH:31]=4)[CH2:25][CH2:24]3)[CH3:19])OCC[O:11]2)=[CH:6][CH:5]=1.Cl.C(=O)(O)[O-].[Na+]>CO>[ClH:36].[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][CH2:22][N:23]2[CH2:24][CH2:25][CH:26]([O:29][C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([Cl:36])[CH:31]=3)[CH2:27][CH2:28]2)[CH3:19])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 20283103HCID 20283103, compound

Product 1

HCID 202831101-{3-{N-[4-(4-Fluorophenyl)-4-oxobutyl]-N-methylamino}propyl}-4-(3-chlorophenoxy)piperidine dihydrochlorideYield 161.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution prepared from 3.36 g (5.96 mmol) of 1-{3-{N-{3-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]propyl}-N-methylamino}propyl}-4-(3-chlorophenoxy)piperidine dihydrochloride, 90 ml of methanol and 40 ml of 3N HCl was heated at reflux under nitrogen for 3 hours. The solution was allowed to cool to room temperature, neutralized with saturated sodium bicarbonate and the methanol evaporated. The residue was made basic with sodium carbonate, extracted twice with ether and washed with saturated sodium chloride. The ether solution was dried over potassium carbonate. Filtration followed by evaporation of the solvent provided an oil. The dihydrochloride was recrystallized from ethanol/methanol to provide 2.50 g (74.4%) of the desired ketone.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen for 3 hours
  3. customthe methanol evaporated
  4. extractionextracted twice with ether
  5. washwashed with saturated sodium chloride
  6. dry with materialThe ether solution was dried over potassium carbonate
  7. filtrationFiltration
  8. customfollowed by evaporation of the solvent
  9. customprovided an oil
  10. customThe dihydrochloride was recrystallized from ethanol/methanol

Sources & evidence

ORD record
ord-51ab6d5b452d41dd98caf5a1024c5777
Source dataset
uspto-grants-1985_05
Patent number
US04518713

Reaction notes

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