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

HRID 463323Notes

Reaction equation

HRID 463323 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]([Cl:35])=[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+].[Na+].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][C:32]([Cl:35])=[CH:31][CH:30]=3)[CH2:26][CH2:27]2)[CH3:19])=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 20283107HCID 20283107, compound

Product 1

HCID 202830801-{2-{N-[4-(4-Fluorophenyl)-4-oxobutyl]-N-methylamino}ethyl}-4-(4-chlorophenoxy)piperidine dihydrochlorideYield 52.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 8.94 g (17.7 mmol) of 1-{2-{N-{3-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]propyl}-N-methylamino}ethyl}-4-(4-chlorophenoxy)piperidine dihydrochloride, 135 ml of methanol, and 55 ml of 3N HCl was heated at reflux for 3 hours under nitrogen. The mixture was allowed to cool to room temperature, poured into saturated sodium carbonate, extracted twice with ether and dried over potassium carbonate. Filtration followed by evaporation of the solvent provided an oil. The yield of a crude dihydrochloride was 6.71 g (81%). Recrystallization from ethanol provided 2.37 g (28%) of the desired ketone.

Workup

  1. temperatureat reflux for 3 hours under nitrogen
  2. extractionextracted twice with ether
  3. dry with materialdried over potassium carbonate
  4. filtrationFiltration
  5. customfollowed by evaporation of the solvent
  6. customprovided an oil
  7. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-4e55e6e76f4440a19cf54d9609105e0e
Source dataset
uspto-grants-1985_05
Patent number
US04518713

Reaction notes

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