Thiochroman → 6-[3-(1-Acetylpiperidin-4-yl)-1-oxopropyl]-3,4-dihydro-2H-1-benzothiopyran

HRID 327401Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 327401
[S:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[CH2:4][CH2:3][CH2:2]1.[C:11]([N:14]1[CH2:19][CH2:18][CH:17]([CH2:20][CH2:21][C:22](Cl)=[O:23])[CH2:16][CH2:15]1)(=[O:13])[CH3:12].[Cl-].[Al+3].[Cl-].[Cl-]>ClCCCl>[C:11]([N:14]1[CH2:15][CH2:16][CH:17]([CH2:20][CH2:21][C:22]([C:9]2[CH:8]=[CH:7][C:6]3[S:1][CH2:2][CH2:3][CH2:4][C:5]=3[CH:10]=2)=[O:23])[CH2:18][CH2:19]1)(=[O:13])[CH3:12]

Komponenten

5

Edukt 3

HCID 137415ThiochromanHCID 6451240Aluminum(III) ChlorideHCID 104659513-(1-Acetyl-4-piperidinyl)propionyl chloride

Produkt 1

HCID 191084806-[3-(1-Acetylpiperidin-4-yl)-1-oxopropyl]-3,4-dihydro-2H-1-benzothiopyranAusbeute 81,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

To a mixture of 3,4-dihydro-2H-1-benzothiopyran (1.5 g) and 3-(1-acetylpiperidin-4-yl)propionyl chloride (2.18 g) in 1,2-dichloroethane (20ml) was added aluminum chloride (3.2 g) portionwise at 10°-15° C. The mixture was stirred at room temperature for 2 hours then refluxed for additional 2 hours, and poured into icewater. The mixture was extracted with dichloromethane, washed with water, dried over anhydrous sodium sulfate. The solvent was distilled off. The residue was purified by silica gel column chromatography (developing solvent: ethyl acetate) to obtain 2.7 g of the title compound as a pale yellow oil.

Aufarbeitung

  1. temperaturethen refluxed for additional 2 hours
  2. additionpoured into icewater
  3. extractionThe mixture was extracted with dichloromethane
  4. washwashed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off
  7. customThe residue was purified by silica gel column chromatography (developing solvent: ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-fcb979243cbd468aaea38beb0bf9cc98
Quelldatensatz
uspto-grants-1993_12
Patentnummer
US05273974

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