Cyanide → 1,1'-Bipiperidine

HRID 1828689

Reaktionsgleichung

Reaktionsgleichung von HRID 1828689
[C-:1]#[N:2].C[Mg+].[Br-].[CH2:6]1[CH2:10]O[CH2:8][CH2:7]1>CCOCC>[N:2]1([N:2]2[CH2:1][CH2:10][CH2:6][CH2:7][CH2:8]2)[CH2:1][CH2:10][CH2:6][CH2:7][CH2:8]1

Komponenten

5

Edukt 3

HCID 5975CyanideHCID 8028TetrahydrofuranHCID 178418689HCID 178418689, Verbindung

Produkt 1

HCID 682791,1'-BipiperidineAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

The cyanide (4.87 g, 15 mmol) was taken up in THF (75 ml). CH3MgBr (25 ml of a 3.0 M solution in Et2O) was added to the reaction mixture at 0° C. The solution was allowed to warm to 25° C. and was stirred at that temperature for 18 h. The solution was partitioned between 25 wt % aqueous solution of sodium citrate and EtOAc. The aqueous layer was extracted with EtOAc. The combined EtOAc layers were washed with brine and dried (Na2SO4). Filtration and concentration gave a yellow oil. Purification via flash chromatography (95/5 to 90/10 EtOAc/MeOH. SiO2) gave 3.7 g (79%) of the piperidino-piperidine 12 as a yellow gum.

Aufarbeitung

  1. customThe solution was partitioned between 25 wt % aqueous solution of sodium citrate and EtOAc
  2. extractionThe aqueous layer was extracted with EtOAc
  3. washThe combined EtOAc layers were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationFiltration and concentration
  6. customgave a yellow oil
  7. customPurification via flash chromatography (95/5 to 90/10 EtOAc/MeOH. SiO2)

Quellen und Nachweise

ORD-Eintrag
ord-c4e3b6ff16c542eb96d78796fd6546bb
Quelldatensatz
uspto-grants-2006_06
Patentnummer
US07060701B2

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