Sodium hydride → tert-Butyl 4-cyano-4-(2,4-dichlorophenyl)piperidine-1-carboxylate

HRID 1066997Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1066997
[C:1]([O:5][C:6](=[O:14])[N:7]([CH2:11][CH2:12]Cl)[CH2:8][CH2:9]Cl)([CH3:4])([CH3:3])[CH3:2].[Cl:15][C:16]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=1[CH2:23][C:24]#[N:25].[H-].[Na+]>CN(C=O)C>[C:1]([O:5][C:6]([N:7]1[CH2:11][CH2:12][C:23]([C:24]#[N:25])([C:17]2[CH:18]=[CH:19][C:20]([Cl:22])=[CH:21][C:16]=2[Cl:15])[CH2:9][CH2:8]1)=[O:14])([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 805662,4-DichlorophenylacetonitrileHCID 11230235N-BOC-N,N-Bis(2-chloroethyl)amine

Produkt 1

HCID 49760258tert-Butyl 4-cyano-4-(2,4-dichlorophenyl)piperidine-1-carboxylateAusbeute 45,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To bis(2-chloroethyl)-carbamic acid tert-butyl ester (1.0 g, 3.8 mmol) and 2,4-dichlorophenyl acetonitrile (0.708 g, 3.8 mmol) in DMF (35 ml), NaH (95%) (0.258 g, 9.68 mmol) was added in one batch at 0° C. The solution was stirred for 10 minutes at room temperature. When foaming subsided, the solution was heated at 60° C. for 24 hours. It was then quenched with water at 0° C. and concentrated. The residue was extracted with ethyl acetate (25 mL) and washed three times with water (15 mL). The organic layer was dried over sodium sulfate, filtered and concentrated. Purification by column chromatography (hexane:ethyl acetate 4:1) yielded 0.620 g (45%) of the product as a syrup.

Aufarbeitung

  1. temperaturethe solution was heated at 60° C. for 24 hours
  2. customIt was then quenched with water at 0° C.
  3. concentrationconcentrated
  4. extractionThe residue was extracted with ethyl acetate (25 mL)
  5. washwashed three times with water (15 mL)
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by column chromatography (hexane:ethyl acetate 4:1)

Quellen und Nachweise

ORD-Eintrag
ord-6fb5428e61214450b5b5ef68a13ac896
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06245773B1

Notizen zur Reaktion

Wird geladen…