Piperidine → 1-[4-(1-Piperidinylsulfonyl)phenyl]ethanone

HRID 507527Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 507527
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10](Cl)(=[O:12])=[O:11])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[NH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.C(N(CC)CC)C>O1CCCC1.[Cl-].[Na+].O>[N:14]1([S:10]([C:7]2[CH:8]=[CH:9][C:4]([C:1](=[O:3])[CH3:2])=[CH:5][CH:6]=2)(=[O:12])=[O:11])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Komponenten

6

Edukt 3

HCID 8082PiperidineHCID 8471TriethylamineHCID 2664184-Acetylbenzenesulfonyl chloride

Produkt 1

HCID 7503641-[4-(1-Piperidinylsulfonyl)phenyl]ethanoneAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

A mixture of 4-acetylbenzene-1-sulfonyl chloride (2 g, 9.2 mmol), piperidine (0.85 g, 10.0 mmol) and triethylamine (1.9 g, 18.4 mmol) in tetrahydrofuran (60 mL) was stirred at rt overnight. Brine (100 mL) was added and the mixture was extracted with ethyl acetate (3×100 mL). The combined organic layer was washed with brine (100 mL), dried over anhydrous sodium sulfate and filtered. Removal of solvent in vacuo gave the title compound as a white solid (2.3 g, 94%). MS (M+H)+ 268.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate (3×100 mL)
  2. washThe combined organic layer was washed with brine (100 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customRemoval of solvent in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-c564f21aa14b4ac3831f7dfe5253d484
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07786132B2

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