Potassium Iodide → 4-[Bis(4-fluorophenyl)methyl]-1-[3-(3,5-dimethoxyphenoxy)propyl]piperidine

HRID 1193675Notes

Reaction equation

HRID 1193675 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:4][CH:3]=1.Cl[CH2:23][CH2:24][CH2:25][O:26][C:27]1[CH:32]=[C:31]([O:33][CH3:34])[CH:30]=[C:29]([O:35][CH3:36])[CH:28]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(O)CCC.C(OCC)(=O)C.C(COC)OC.CCCCCC.C(OCC)(=O)C>[F:21][C:18]1[CH:17]=[CH:16][C:15]([CH:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[CH:9]2[CH2:14][CH2:13][N:12]([CH2:23][CH2:24][CH2:25][O:26][C:27]3[CH:32]=[C:31]([O:33][CH3:34])[CH:30]=[C:29]([O:35][CH3:36])[CH:28]=3)[CH2:11][CH2:10]2)=[CH:20][CH:19]=1

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 132505444-[Bis(4-fluorophenyl)methyl]piperidineHCID 144071741-(3-Chloropropoxy)-3,5-dimethoxybenzene

Product 1

HCID 144070944-[Bis(4-fluorophenyl)methyl]-1-[3-(3,5-dimethoxyphenoxy)propyl]piperidine

Reagents, catalysts & solvents 3

HCID 2631-ButanolSolventHCID 21226206Ethyl acetate hexaneSolventHCID 87198031Ethyl acetate dimethoxyethaneSolvent

Procedure

A mixture of 5.51 g (0.019 mole) of 4-[bis(4-fluorophenyl)methyl]piperidine, 4.42 g (0.019 mole) of 1-(3-chloropropoxy)-3,5-dimethoxybenzene and potassium carbonate (5.53 g, 0.04 mole) was heated overnight at reflux in 350 ml of 1-butanol containing potassium iodide (0.3 g). The reaction mixture was stripped to dryness and the residue partitioned between chloroform-5% sodium hydroxide and chloroform-water. Removal of chloroform gave a brown oil. The oil was subjected to chromatography on a silica gel column using a gradient elution series of hexane-ethyl acetate and ethyl acetate-dimethoxyethane. After combining proper fractions eluted from the column and removing solvent, the residual oil was dried in vacuo overnight at 80° C. This produced 2.61 g (28.5%) of brown oil.

Workup

  1. temperaturewas heated overnight
  2. customthe residue partitioned between chloroform-5% sodium hydroxide and chloroform-water
  3. customRemoval of chloroform
  4. customgave a brown oil
  5. washeluted from the column
  6. customremoving solvent
  7. customthe residual oil was dried in vacuo overnight at 80° C

Sources & evidence

ORD record
ord-c3ca385633b04030a9eae1086601ef75
Source dataset
uspto-grants-1989_03
Patent number
US04810713

Reaction notes

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