Diethyl Ether → 1-(Aminomethyl)cyclohexan-1-ol

HRID 375887

Reaktionsgleichung

Reaktionsgleichung von HRID 375887
Cl.[NH2:2][CH2:3][C:4]1([OH:10])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.C([O-])([O-])=O.[K+].[K+].CCOCC>O>[NH2:2][CH2:3][C:4]1([OH:10])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1

Komponenten

5

Edukt 3

HCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 3084332Cyclohexanol, 1-(aminomethyl)-, hydrochloride (1:1)

Produkt 1

HCID 776141-(Aminomethyl)cyclohexan-1-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

1-Aminomethyl-1-cyclohexanol hydrochloride (1 g, 6.04 mmol) was dissolved in cold water and then K2CO3 and ether were added. The mixture was stirred and then the ether layer was separated and the aqueous layer was again extracted with ether. The ether layers were combined, dried over MgSO4 and concentrated to afford 1-aminomethyl-1-cyclohexanol which was mixed with DMSO (3 mL) and 1-ethyl-6-methoxy-1H-pyrazolo[3,4-b]quinoline (0.8 g, 3 mmol). The reaction mixture was stirred at 110° C. overnight and then was partitioned between water and CH2Cl2. The CH2Cl2 layer was separated, dried, filtered and evaporated. The residue was crystallized from CH2Cl2 and recrystallized from acetonitrile to afford 0.65 g of 1-ethyl-6-methoxy-N-[(1-hydroxycyclohexyl)methyl]-1H-pyrazolo[3,4-b]quinolin-4-amine, m.p. 201-°203° C.

Aufarbeitung

  1. customthe ether layer was separated
  2. extractionthe aqueous layer was again extracted with ether
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-b9d66a9f33694304ab9e32953c674d1b
Quelldatensatz
uspto-grants-1996_01
Patentnummer
US05488055

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