Ethyl 1-cyanocyclohexane-1-carboxylate → Ethyl 1-(aminomethyl)cyclohexane-1-carboxylate

HRID 2366739Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2366739
[C:1]([C:3]1([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1)#[N:2]>Cl.C(O)C.[Pt](=O)=O>[NH2:2][CH2:1][C:3]1([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

Komponenten

5

Edukt 1

HCID 10997650Ethyl 1-cyanocyclohexane-1-carboxylate

Produkt 1

HCID 21840381Ethyl 1-(aminomethyl)cyclohexane-1-carboxylateAusbeute 32,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 345198Adams' catalystKatalysatorHCID 313Hydrochloric AcidLösungsmittelHCID 702EthanolLösungsmittel

Versuchsvorschrift

Platinum (IV) oxide (1.72 g) was added to a solution of ethyl 1-cyanocyclohexanecarboxylate (17.15 g, 94.6 mmol) in concentrated hydrochloric acid (20 mL) and ethanol (200 mL), and the mixture was placed under hydrogen pressure on a Parr apparatus and shaken for 20 hours. The solvent was removed under reduced pressure, and the residue was diluted with water. The resulting mixture was adjusted to pH 7 with the addition of solid sodium carbonate and then extracted several times with dichloromethane. The combined extracts were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide 5.67 g of ethyl 1-(aminomethyl)cyclohexanecarboxylate as a colorless oil. A portion of the water was removed from the aqueous layer, and dichloromethane was added. The mixture was stirred overnight at ambient temperature, and the organic fraction was separated, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide 11.69 g of ethyl 1-(aminomethyl)cyclohexanecarboxylate hydrochloride as a white solid.

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. additionthe residue was diluted with water
  3. additionThe resulting mixture was adjusted to pH 7 with the addition of solid sodium carbonate
  4. extractionextracted several times with dichloromethane
  5. dry with materialThe combined extracts were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c3b6920977384faaa7aa6f5cc6842bc0
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08697873B2

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