Potassium Iodide → 1-[3-(6-Fluoro-1,2-benzisoxazol-3-yl)propyl]-4-(N-propionylanilino)piperidine hydrochloride

HRID 280889노트

반응식

HRID 280889 반응식
[Cl:1][CH2:2][CH2:3][CH2:4][C:5]1[C:9]2[CH:10]=[CH:11][C:12]([F:14])=[CH:13][C:8]=2[O:7][N:6]=1.[C:15]([N:19]([CH:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)(=[O:18])[CH2:16][CH3:17].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O>[ClH:1].[F:14][C:12]1[CH:11]=[CH:10][C:9]2[C:5]([CH2:4][CH2:3][CH2:2][N:29]3[CH2:28][CH2:27][CH:26]([N:19]([C:15](=[O:18])[CH2:16][CH3:17])[C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH2:31][CH2:30]3)=[N:6][O:7][C:8]=2[CH:13]=1

참가 물질

6

반응물 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 2593814-(N-Propionylaniline)piperidineHCID 109108803-(3-Chloropropyl)-6-fluorobenzo[d]isoxazole

생성물 1

HCID 133198601-[3-(6-Fluoro-1,2-benzisoxazol-3-yl)propyl]-4-(N-propionylanilino)piperidine hydrochloride수율 55%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of 9.8 g of 3-(3-chloropropyl)-6-fluoro-1,2-benzisoxazole, 10 g of 4-(N-propionylanilino)piperidine, 7.1 g potassium carbonate, and a few crystals potassium iodide in 125 ml of dimethylformamide was stirred at 75° C. for three hrs. The reaction mixture was cooled, filtered and concentrated to an oil. The oil was stirred with water and extracted with ether. The organic extracts were washed with water (2x), saturated sodium chloride solution and dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was treated with ethereal hydrogen chloride to give 10 g (55%) of product, mp 155°-160° C.

후처리

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered
  3. concentrationconcentrated to an oil
  4. extractionextracted with ether
  5. washThe organic extracts were washed with water (2x), saturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. additionThe residue was treated with ethereal hydrogen chloride

출처 및 근거

ORD 기록
ord-845f926ce49c462fbebd84dc604d4281
출처 데이터셋
uspto-grants-1986_05
특허 번호
US04591586

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