Acetonitrile → 6-Fluoro-3-[1-(3-phenoxypropyl)-4-piperidinyl]1,2-benzisoxazole

HRID 264155

반응식

HRID 264155 반응식
[F:1][C:2]1[CH:16]=[CH:15][C:5]2[C:6]([CH:9]3[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]3)=[N:7][O:8][C:4]=2[CH:3]=1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:24][CH2:25][CH2:26][O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(#N)C>O>[F:1][C:2]1[CH:16]=[CH:15][C:5]2[C:6]([CH:9]3[CH2:10][CH2:11][N:12]([CH2:24][CH2:25][CH2:26][O:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH2:13][CH2:14]3)=[N:7][O:8][C:4]=2[CH:3]=1

참가 물질

6

반응물 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 76917(3-Chloropropoxy)benzeneHCID 8494213-(4-Piperidyl)-6-fluoro-1,2-benzisoxazole

생성물 1

HCID 104733206-Fluoro-3-[1-(3-phenoxypropyl)-4-piperidinyl]1,2-benzisoxazole수율 47%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (4.0 g, 18.2 mmol), K2CO3 (3.0 g, 21.8 mmol), KI (100 mg), 3-chloropropoxybenzene (3.4 g, 20.0 mmol), and acetonitrile was stirred at reflux under nitrogen for 30 hours. The reaction was poured into water and the aqueous mixture was extracted with ethyl acetate. The ethyl acetate extract was washed with brine, dried with MgSO4 and concentrated to afford 6.2 g of a damp, beige solid. The compound was recrystallized twice from ethanol to yield (47%) of 6-fluoro-3-[1-(3-phenoxypropyl)-4-piperidinyl]-1,2-benzisoxazole as a light beige solid, m.p.=78°-80° C.

후처리

  1. temperatureat reflux under nitrogen for 30 hours
  2. extractionthe aqueous mixture was extracted with ethyl acetate
  3. extractionThe ethyl acetate extract
  4. washwas washed with brine
  5. dry with materialdried with MgSO4
  6. concentrationconcentrated
  7. customto afford 6.2 g of a damp, beige solid
  8. customThe compound was recrystallized twice from ethanol

출처 및 근거

ORD 기록
ord-6a46efa659a945a4b001f02e746b9cfc
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05646161

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