Dimethylformamide → 1-[4-[4-[4-(6-Fluoro1,2-benzisoxazol-3-yl)-1-piperidinyl]butoxy]-3-methoxyphenyl]ethanone

HRID 266937노트

반응식

HRID 266937 반응식
Cl.[F:2][C:3]1[CH:17]=[CH:16][C:6]2[C:7]([CH:10]3[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]3)=[N:8][O:9][C:5]=2[CH:4]=1.[C:18]([O-])([O-])=O.[K+].[K+].Br[CH2:25][CH2:26][CH2:27][CH2:28][O:29][C:30]1[CH:35]=[CH:34][C:33]([CH:36]=[O:37])=[CH:32][C:31]=1[O:38][CH3:39].CN(C)C=O>O>[F:2][C:3]1[CH:17]=[CH:16][C:6]2[C:7]([CH:10]3[CH2:11][CH2:12][N:13]([CH2:25][CH2:26][CH2:27][CH2:28][O:29][C:30]4[CH:35]=[CH:34][C:33]([C:36](=[O:37])[CH3:18])=[CH:32][C:31]=4[O:38][CH3:39])[CH2:14][CH2:15]3)=[N:8][O:9][C:5]=2[CH:4]=1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 11334359R-56109 hydrochlorideHCID 190306744-(4-Bromobutoxy)-3-methoxybenzaldehyde

생성물 1

HCID 100947901-[4-[4-[4-(6-Fluoro1,2-benzisoxazol-3-yl)-1-piperidinyl]butoxy]-3-methoxyphenyl]ethanone수율 87.4%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
75 °C

실험 절차

A stirred mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole hydrochloride (5.1 g, 0.02 mol), K2CO3 (5.2 g, 0.04 mol), 1-[4-(4-bromobutoxy)-3-methoxyphenyl]methanone (6.6 g, 22 mmol), and dimethylformamide (60 ml) was heated at 75° C. for 5 hours. The reaction was poured into water, and the aqueous mixture was extracted with ethyl acetate. The ethyl acetate was washed (water), dried (MgSO4), and the solvent was concentrated to yield initially an oil, which solidified upon standing. The solid was triturated with hexane and collected to afford 7.7 g of the product as a waxy solid. The compound was chromatographed on a Waters Prep 500 utilizing silica gel columns and eluting with dichloromethane/methanol (5%). Concentration of the appropriate fractions yielded 5.1 g of off-white solid 1-[4-[4-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]-butoxy]-3-methoxyphenyl]ethanone, which when recrystallized from ethyl alcohol yielded 3.2 g (36%) of feathery-white needles, m.p.=88°-90° C.

후처리

  1. extractionthe aqueous mixture was extracted with ethyl acetate
  2. washThe ethyl acetate was washed (water)
  3. dry with materialdried (MgSO4)
  4. concentrationthe solvent was concentrated
  5. customto yield initially an oil, which
  6. customThe solid was triturated with hexane
  7. customcollected

출처 및 근거

ORD 기록
ord-48f029fd59384ba28d8eacb0e1d9cb48
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05652241

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