Potassium Carbonate → 1-[3-(6-Fluoro-1,2-benzisoxazol-3-yl)propyl]-4-(3-phenylpropyl)piperidine hydrochloride

HRID 280885

반응식

HRID 280885 반응식
[C:1]1([CH2:7][CH2:8][CH2:9][CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:16][CH2:17][CH2:18][CH2:19][C:20]1[C:24]2[CH:25]=[CH:26][C:27]([F:29])=[CH:28][C:23]=2[O:22][N:21]=1.C(=O)([O-])[O-].[K+].[K+]>[I-].[K+].CN(C)C=O>[ClH:16].[F:29][C:27]1[CH:26]=[CH:25][C:24]2[C:20]([CH2:19][CH2:18][CH2:17][N:13]3[CH2:12][CH2:11][CH:10]([CH2:9][CH2:8][CH2:7][C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[CH2:15][CH2:14]3)=[N:21][O:22][C:23]=2[CH:28]=1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 876784-(3-Phenylpropyl)piperidineHCID 109108803-(3-Chloropropyl)-6-fluorobenzo[d]isoxazole

생성물 1

HCID 133198541-[3-(6-Fluoro-1,2-benzisoxazol-3-yl)propyl]-4-(3-phenylpropyl)piperidine hydrochloride수율 75.3%

시약·촉매·용매 2

HCID 4875Potassium Iodide촉매HCID 6228Dimethylformamide용매

반응 조건

온도
90 °C

실험 절차

To 40 ml of dimethylformamide was added 4.06 g of 4-(3-phenylpropyl)piperidine, 3.4 g of 3-(3-chloropropyl)-6-fluoro-1,2-benzisoxazole, 10 g of milled potassium carbonate, and 0.01 g of potassium iodide. After stirring at 90° C. for three hrs, the mixture was cooled, filtered and the filtrate was evaporated to an oil. The oil was stirred with 100 ml of water for ten mins and then extracted with ether. The ether extract was washed with water (2x), saturated sodium chloride solution and dried over anhydrous magnesium sulfate. After filtering, the solution was acidified to pH 1 with ethereal hydrogen chloride. The resultant precipitate was collected and dried to give 5.0 g (60%) of product, mp 95° C. Recrystallization from ethyl acetate/methanol (5:1) gave the analytical sample, mp 136°-137° C.

후처리

  1. temperaturethe mixture was cooled
  2. filtrationfiltered
  3. customthe filtrate was evaporated to an oil
  4. stirringThe oil was stirred with 100 ml of water for ten mins
  5. extractionextracted with ether
  6. extractionThe ether extract
  7. washwas washed with water (2x), saturated sodium chloride solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationAfter filtering
  10. customThe resultant precipitate was collected
  11. customdried

출처 및 근거

ORD 기록
ord-5e59c6e8b46a4e1daaf822fe8670eaec
출처 데이터셋
uspto-grants-1986_05
특허 번호
US04591586

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