Potassium Iodide → 1-[3-(6-Fluoro-1,2-benzisoxazol-3-yl)propyl]-4-phenylpiperazine oxalate

HRID 64613노트

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HRID 64613 반응식
[C:1]1([N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[CH2:14][CH2:15][CH2:16][C:17]1[C:21]2[CH:22]=[CH:23][C:24]([F:26])=[CH:25][C:20]=2[O:19][N:18]=1.[C:27](=[O:30])([OH:29])[O-].[Na+].[I-].[K+].CN(C)C=[O:37]>>[C:20]([OH:19])(=[O:37])[C:27]([OH:29])=[O:30].[F:26][C:24]1[CH:23]=[CH:22][C:21]2[C:17]([CH2:16][CH2:15][CH2:14][N:10]3[CH2:11][CH2:12][N:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[CH2:8][CH2:9]3)=[N:18][O:19][C:20]=2[CH:25]=1

참가 물질

6

반응물 5

HCID 4875Potassium IodideHCID 6228DimethylformamideHCID 70961-PhenylpiperazineHCID 516892Sodium BicarbonateHCID 109108803-(3-Chloropropyl)-6-fluorobenzo[d]isoxazole

생성물 1

HCID 135207311-[3-(6-Fluoro-1,2-benzisoxazol-3-yl)propyl]-4-phenylpiperazine oxalate

반응 조건

온도
100 °C

실험 절차

To 35 ml of dry dimethylformamide was added 1.6 g of 4-phenylpiperazine, 2.1 g of 3-(3-chloropropyl)-6-fluoro-1,2-benzisoxazole, 8.0 g of sodium bicarbonate, and a few crystals of potassium iodide. The mixture was heated at 100° C. for three hrs, with stirring. The mixture was filtered and the filtrate was evaporated to an oil. The oil was stirred with 100 ml of water for five mins and then extracted with ether. The ether extract was washed with water (2×), saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. After filtering, the solution was converted to 4.0 g (70%) of product, by treatment with ethereal oxalic acid. Recrystallization twice from ethyl acetate/methanol/ether yielded the analytical sample mp 188°-190° C. (dec).

후처리

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated to an oil
  3. stirringThe oil was stirred with 100 ml of water for five mins
  4. extractionextracted with ether
  5. extractionThe ether extract
  6. washwas washed with water (2×), saturated sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationAfter filtering
  9. customRecrystallization twice from ethyl acetate/methanol/ether
  10. customyielded the analytical sample mp 188°-190° C. (dec)

출처 및 근거

ORD 기록
ord-d16ef50e04834e06baec5083ad8bc421
출처 데이터셋
uspto-grants-1986_09
특허 번호
US04609658

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