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

HRID 1792647노트

반응식

HRID 1792647 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)-1,2benzisoxazole (2.2 g, 0.01 mole), 1-[4-(3-chloropropoxy)-3-methoxyphenyl]ethanone (24g, 0.01 mole), K2CO3 (1.4 g), a few crystals of KI and acetonitrile (100 ml) was stirred and refluxed for 8hours. 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 8hours
  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-68ec85c7a1cc4ffd9adfdabb5d2c3bb4
출처 데이터셋
uspto-grants-2006_07
특허 번호
USRE039198E1

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