Hydrochloric Acid → 1-{N-{3-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]propyl}-N-methylaminoacetyl}-4-phenoxypiperidine oxalate

HRID 463317Notes

Reaction equation

HRID 463317 reaction equation
[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].[F:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2([CH2:19][CH2:20][CH2:21][N:22]([CH2:24][C:25]([N:27]3[CH2:32][CH2:31][CH:30]([O:33][C:34]4[CH:39]=[CH:38][CH:37]=[C:36](Cl)[CH:35]=4)[CH2:29][CH2:28]3)=[O:26])[CH3:23])[O:18][CH2:17][CH2:16][O:15]2)=[CH:10][CH:9]=1.Cl.[H][H]>[Pd].CO>[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].[F:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2([CH2:19][CH2:20][CH2:21][N:22]([CH2:24][C:25]([N:27]3[CH2:28][CH2:29][CH:30]([O:33][C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=4)[CH2:31][CH2:32]3)=[O:26])[CH3:23])[O:15][CH2:16][CH2:17][O:18]2)=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 202831291-{N-{3-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]propyl}-N-methylaminoacetyl}-4-(3-chlorophenoxy)piperidine oxalateHCID 178418361HCID 178418361, compound

Product 1

HCID 202831161-{N-{3-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]propyl}-N-methylaminoacetyl}-4-phenoxypiperidine oxalateYield 45%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 1.0 g (1.72 mmol) of 1-{N-{3-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]propyl}-N-methylaminoacetyl}-4-(3-chlorophenoxy)piperidine oxalate, 0.3 g of 5% palladium on carbon, 40 ml methanol and 0.02 ml of saturated methanolic hydrogen chloride was heated at 50° under 50 psi hydrogen for 4 hours and allowed to cool to room temperature. The mixture was filtered and the methanol evaporated. The residue was dissolved in ether, washed with saturated sodium carbonate and saturated sodium chloride, and dried over potassium carbonate. Filtration followed by evaporation of the solvent provided an oil. The oxalate was recrystallized from ethanol to provide 0.42 g (45%) of 1-{N-{3-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]propyl}-N-methylaminoacetyl}-4-phenoxypiperidine oxalate.

Workup

  1. filtrationThe mixture was filtered
  2. customthe methanol evaporated
  3. dissolutionThe residue was dissolved in ether
  4. washwashed with saturated sodium carbonate and 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 oxalate was recrystallized from ethanol

Sources & evidence

ORD record
ord-1ca9dbea3b5e4f8286feff601a2650bc
Source dataset
uspto-grants-1985_05
Patent number
US04518713

Reaction notes

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