Hydrochloric Acid → 3-Aminomethyl-6-cyclohexylmethyl-pyridine

HRID 2041525Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2041525
Cl.C(OC([NH:9][CH2:10][C:11]1[CH:12]=[N:13][C:14]([CH2:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=[CH:15][CH:16]=1)=O)(C)(C)C.CCCCCC>O1CCOCC1.CCOC(C)=O>[NH2:9][CH2:10][C:11]1[CH:12]=[N:13][C:14]([CH2:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=[CH:15][CH:16]=1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 576559013-Tert-butoxycarbonylaminomethyl-6-cyclohexylmethyl-pyridine

Produkt 1

HCID 576566033-Aminomethyl-6-cyclohexylmethyl-pyridineAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Add 4N hydrogen chloride in dioxane (10 mL) to a solution of 3-tert-butoxycarbonylaminomethyl-6-cyclohexylmethyl-pyridine (345 mg, 1.13 mmol) in EtOAc (10 mL) and stir overnight. Concentrate in vacuo, suspend the solid obtained in diethyl ether and add hexane. Filter and wash the solid with hexane. Suspend the solid into dichloromethane, add saturated aqueous NaHCO3 and stir until both phases are clear (15 min). Extract the aqueous phase twice with dichoromethane. Dry the combined organic extracts over MgSO4, filter and concentrate in vacuo to obtain the title compound as an oil (205 mg, 97%) that was used without any further purification. MS (ES+) n7/z: 205 (M+H)+.

Aufarbeitung

  1. concentrationConcentrate in vacuo
  2. customobtained in diethyl ether
  3. filtrationFilter
  4. washwash the solid with hexane
  5. additionadd saturated aqueous NaHCO3
  6. stirringstir until both phases
  7. custom(15 min)
  8. extractionExtract the aqueous phase twice with dichoromethane
  9. dry with materialDry the combined organic extracts over MgSO4
  10. filtrationfilter
  11. concentrationconcentrate in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-681bc10dd7f844428b852803deb0f9f8
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08580780B2

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