Toluene → 1-[2-(Bis-(4-fluorophenyl)-methoxy)-ethyl]-4-(3-phenyloxadiazol-5-yl-methyl)piperazine

HRID 1197513

Reaction equation

HRID 1197513 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.C1(C2N=[C:34]([CH2:36]Cl)[O:33][N:32]=2)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].[C:44]1(C)[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1.C[N:52]([CH3:55])C=O>O>[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]([CH2:36][C:34]3[O:33][NH:32][N:52]([C:44]4[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=4)[CH:55]=3)[CH2:14][CH2:13]2)=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 1140TolueneHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 9667145-(Chloromethyl)-3-phenyl-1,2,4-oxadiazoleHCID 99740131-[2-[Bis(4-fluorophenyl)methoxy]ethyl]piperazine

Product 1

HCID 191067401-[2-(Bis-(4-fluorophenyl)-methoxy)-ethyl]-4-(3-phenyloxadiazol-5-yl-methyl)piperazine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.08 g (3.3 mM) of 1-[2-(bis-(4-fluorophenyl)-methoxy)ethyl]piperazine and 0.97 g of 3-phenyl-5-chloromethyl-1,2,4-oxadiazole (prepared according to Chem.Ber. 105 (1972)2825) were dissolved in 5 ml of dry dimethylformamide. 1.4 g of potassium carbonate were added and the mixture was stirred at room temperature overnight. Toluene and water were added, the aqueous phase extracted with toluene, the combined organic phases washed three times with water, treated with charcoal and evaporated in vacuo. The residue was dissolved in 10 ml of ethanol and 0.69 g of maleic acid were added. The precipitate was isolated by filtration and recrystallized from hot acetonitrile to obtain the dimaleate salt of the title compound as colourless crystals melting at 142°-143°. Analytical data were in accordance with the proposed structure.

Workup

  1. extractionthe aqueous phase extracted with toluene
  2. washthe combined organic phases washed three times with water
  3. additiontreated with charcoal
  4. customevaporated in vacuo
  5. dissolutionThe residue was dissolved in 10 ml of ethanol
  6. addition0.69 g of maleic acid were added
  7. customThe precipitate was isolated by filtration
  8. customrecrystallized from hot acetonitrile

Sources & evidence

ORD record
ord-a9aa31526e9e43b3be5fba1f02c9e189
Source dataset
uspto-grants-1994_01
Patent number
US05276035

Linked notes

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