Potassium Carbonate → HCID 20443032, compound

HRID 1632483Notes

Reaction equation

HRID 1632483 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[O:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[CH:4][CH:3]=1.[Cl:25][CH2:26][CH2:27][CH2:28][C:29]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:30].C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C(C)C>[ClH:25].[ClH:25].[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:18]2[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=2)[O:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][N:15]([CH2:26][CH2:27][CH2:28][C:29]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[O:30])[CH2:14][CH2:13]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2535334-ChlorobutyrophenoneHCID 99740131-[2-[Bis(4-fluorophenyl)methoxy]ethyl]piperazine

Product 1

HCID 20443032HCID 20443032, compound

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 6 g (0.018 mol) of 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]piperazine, 6.6 g (0.036 mol) of 4-chloro-1-phenyl-1-butanone and 5 g of powdered potassium carbonate in 100 ml of methyl isobutyl ketone was refluxed for 6 hours with stirring. The reaction mixture was concentrated by evaporation of the solvent and water and diethyl ether were added to the residue, after which the ethereal layer was separated off, washed with water, dried on sodium sulfate and the solvent was evaporated. The residue obtained was purified by columnchromatography (silicagel, eluent: chloroform/methanol 9:1). The proper fractions were concentrated and the residue was taken up in anhydrous diethyl ether, after which the solution was carefully acidified with a solution of hydrogen chloride in diethyl ether to pH=2. The precipitate obtained of 4-[4-[2-[bis(4-fluorophenyl)methoxy]-ethyl]-1-piperazinyl]-1-phenyl-1-butanone dihydrochloride was filtered off and crystallized once from 2-propanol.

Workup

  1. temperaturewas refluxed for 6 hours
  2. concentrationThe reaction mixture was concentrated by evaporation of the solvent and water and diethyl ether
  3. additionwere added to the residue
  4. customafter which the ethereal layer was separated off
  5. washwashed with water
  6. customdried on sodium sulfate
  7. customthe solvent was evaporated
  8. customThe residue obtained
  9. customwas purified by columnchromatography (silicagel, eluent: chloroform/methanol 9:1)
  10. concentrationThe proper fractions were concentrated

Sources & evidence

ORD record
ord-9204cdb06f154896913deda286011544
Source dataset
uspto-grants-1984_10
Patent number
US04476129

Reaction notes

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