Acetonitrile → 1-[4-[3-[4-(5-Fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]propoxy]-3-methoxyphenyl]ethanone

HRID 2257602

반응식

HRID 2257602 반응식
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][N:8]=[C:7]([CH:10]3[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]3)[C:6]=2[CH:16]=1.Cl[CH2:18][CH2:19][CH2:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([C:28](=[O:30])[CH3:29])=[CH:24][C:23]=1[O:31][CH3:32].C([O-])([O-])=O.[K+].[K+].C(#N)C>O>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][N:8]=[C:7]([CH:10]3[CH2:11][CH2:12][N:13]([CH2:18][CH2:19][CH2:20][O:21][C:22]4[CH:27]=[CH:26][C:25]([C:28](=[O:30])[CH3:29])=[CH:24][C:23]=4[O:31][CH3:32])[CH2:14][CH2:15]3)[C:6]=2[CH:16]=1

참가 물질

6

반응물 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 27947555-Fluoro-3-(4-piperidinyl)-1,2-benzisoxazoleHCID 73142644-(3-Chloropropoxy)-3-methoxyacetophenone

생성물 1

HCID 103202521-[4-[3-[4-(5-Fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]propoxy]-3-methoxyphenyl]ethanone수율 93.8%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A mixture of 5-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (2.2 g, 0.01 mole), 1-[4-(3-chloropropoxy)-3-methoxyphenyl]ethanone (2.4 g, 0.01 mole), K2CO3 (1.4 g), a few crystals of KI and acetonitrile (100 ml) was stirred and refluxed for 8 hours. The reaction was poured into water and the aqueous mixture was extracted with ethyl acetate. The ethyl acetate extract was washed (brine), dried (MgSO4), and concentrated to afford 4.0 g of a white solid. The solid was chromatographed on a Waters Prep 500 HPLC utilizing silica gel columns and eluting with methylene chloride/methanol (5%). Concentration of the appropriate fractions afforded 2.0 g (47%) of 1-[4-[3-[4-(5-fluoro-1,2-benzisoxazol-3-yl-1-piperidinyl]propoxy]-3-methoxyphenyl]ethanone as a white crystalline solid, m.p.=103°-105° C.

후처리

  1. temperaturerefluxed for 8 hours
  2. extractionthe aqueous mixture was extracted with ethyl acetate
  3. extractionThe ethyl acetate extract
  4. washwas washed (brine)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-e116e7400e994755ad68df9fa2c0f766
출처 데이터셋
uspto-grants-1997_08
특허 번호
US05658911

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