2-Fluoro-5-methylbenzonitrile → N-(2-Cyano-4-methylphenyl)-4-piperidone propylene ketal

HRID 842782Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 842782
F[C:2]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:3]=1[C:4]#[N:5].[CH2:11]1[O:21][C:15]2([CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)[O:14][CH:12]1[CH3:13]>CN(C=O)C.CCOCC.C(=O)([O-])[O-].[Na+].[Na+]>[CH2:11]1[O:21][C:15]2([CH2:20][CH2:19][N:18]([C:2]3[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:3]=3[C:4]#[N:5])[CH2:17][CH2:16]2)[O:14][CH:12]1[CH3:13]

Komponenten

6

Edukt 2

HCID 27745842-Fluoro-5-methylbenzonitrileHCID 129541174-Piperidone propylene ketal

Produkt 1

HCID 86757963N-(2-Cyano-4-methylphenyl)-4-piperidone propylene ketal

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 10340Sodium CarbonateLösungsmittel

Versuchsvorschrift

A solution of 2-fluoro-5-methylbenzonitrile (2.76 g, 20.4 mmol) and 4-piperidone propylene ketal (3.39 g, 21.5 mmol) in DMF (50 mL) was heated in an oil bath (90° C., 20 h). The mixture was diluted with ether and sodium carbonate solution. The aqueous layer was extracted with two additional portions of ether and the combined organic extracts were washed with brine, dried over Na2SO4, and concentrated under reduced pressure. PCTLC (SiO2, 6 mm, 50-0% hexane/CHCl3) afforded the title compound (29).

Aufarbeitung

  1. extractionThe aqueous layer was extracted with two additional portions of ether
  2. washthe combined organic extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-2ca31ef732be4aaaa27a5267183f06eb
Quelldatensatz
uspto-grants-2002_04
Patentnummer
US06376503B1

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