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Water → 6-[3-(4-(4-fluorobenzoyl)-1-piperidyl)propyl]-6H-dibenzo[c,e]-1,2-thiazine 5,5-dioxide

HRID 654104
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HRID 654104 반응식
[CH:1]1[C:6]2[C:7]3[CH:16]=[CH:15][CH:14]=[CH:13][C:8]=3[NH:9][S:10](=[O:12])(=[O:11])[C:5]=2[CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Cl[CH2:20][CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][CH:26]([C:29](=[O:37])[C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=2)[CH2:25][CH2:24]1.O>CN(C)C=O.C(OCC)(=O)C>[F:36][C:33]1[CH:32]=[CH:31][C:30]([C:29]([CH:26]2[CH2:27][CH2:28][N:23]([CH2:22][CH2:21][CH2:20][N:9]3[C:8]4[CH:13]=[CH:14][CH:15]=[CH:16][C:7]=4[C:6]4[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=4[S:10]3(=[O:12])=[O:11])[CH2:24][CH2:25]2)=[O:37])=[CH:35][CH:34]=1
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참가 물질

7

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 7080916~{h}-Benzo[c][1,2]benzothiazine 5,5-DioxideHCID 12404419[1-(3-Chloropropyl)piperidin-4-yl](4-fluorophenyl)methanone

생성물 1

HCID 198884636-[3-(4-(4-fluorobenzoyl)-1-piperidyl)propyl]-6H-dibenzo[c,e]-1,2-thiazine 5,5-dioxide수율 51.2%

시약·촉매·용매 2

HCID 6228
Dimethylformamide
용매
3회
HCID 8857Ethyl Acetate용매

반응 조건

온도
100 °C

실험 절차

A solution of 6H-dibenzo[c,e]-1,2-thiazine 5,5-dioxide (1.7 g) in dry N,N-dimethylformamide (15 cc) is added dropwise to a suspension of sodium hydride (0.25 g, 80% suspension in oil) in N,N-dimethylformamide (5 cc). After 30 minutes' stirring, a solution of 1-(3-chloropropyl)-4-(4-fluorobenzoyl)piperidine (2.1 g) in N,N-dimethylformamide (15 cc) is added. The reaction mixture is heated to 100° C. for 40 minutes and is then cooled and poured into a mixture of water (150 cc) and ethyl acetate (150 cc). The organic phase is washed with water (3×50 cc), is dried over magnesium sulphate and is concentrated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed on a column of silica gel (0.06-0.2-mm particle size, 2-cm diameter, 25-cm height) and eluted with a mixture of cyclohexane and ethyl acetate (50--50 by volume), 30-cc fractions being collected; fractions 7 to 16 are combined and concentrated to dryness under reduced pressure (2.7 kPa). The residue is recrystallized from ethanol (40 cc); the crystals obtained are filtered off, washed with ethanol (5 cc) and dried. 6-[3-(4-(4-fluorobenzoyl)-1-piperidyl)propyl]-6H-dibenzo[c,e]-1,2-thiazine 5,5-dioxide (1.8 g) is obtained, melting at 114° C.

후처리

  1. temperatureis then cooled
  2. washThe organic phase is washed with water (3×50 cc)
  3. dry with materialis dried over magnesium sulphate
  4. concentrationis concentrated to dryness under reduced pressure (2.7 kPa)
  5. customThe residue is chromatographed on a column of silica gel (0.06-0.2-mm particle size, 2-cm diameter, 25-cm height)
  6. washeluted with a mixture of cyclohexane and ethyl acetate (50--50 by volume), 30-cc fractions
  7. custombeing collected
  8. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  9. customThe residue is recrystallized from ethanol (40 cc)
  10. customthe crystals obtained
  11. filtrationare filtered off
  12. washwashed with ethanol (5 cc)
  13. customdried

출처 및 근거

ORD 기록
ord-2d14d187092c47d9a0a35feae7a26986
출처 데이터셋
uspto-grants-1992_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05130313

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