StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

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

HRID 654104
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 654104
[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
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 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

Produkt 1

HCID 198884636-[3-(4-(4-fluorobenzoyl)-1-piperidyl)propyl]-6H-dibenzo[c,e]-1,2-thiazine 5,5-dioxideAusbeute 51,2 %

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 6228DimethylformamideLösungsmittel3×HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-2d14d187092c47d9a0a35feae7a26986
Quelldatensatz
uspto-grants-1992_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05130313

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion