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

HRID 1197513

반응식

HRID 1197513 반응식
[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

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a9aa31526e9e43b3be5fba1f02c9e189
출처 데이터셋
uspto-grants-1994_01
특허 번호
US05276035

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