Reaktion #809213

Reaktionsgleichung

sodium hydrogencarbonate

N-tert-butoxycarbonyl-trans-1,4-cyclohexanediamine

3-pyridinecarboxylic acid

1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide

1-hydroxybenzotriazole

→

N-tert-butoxycarbonyl-trans-4-(3-pyridylcarbonylamino)cyclohexylamine

Lösungsmittel

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe resulting mixture was extracted with ethyl acetate
2. 2
   WaschenThe extract was washed with brine
3. 3
   Trocknendried over anhydrous sodium sulfate
4. 4
   Sonstigethe solvent was removed under reduced pressure
5. 5
   WaschenThe residue was washed with diethyl ether

Vorschrift

10 ml of a N,N-dimethylformamide solution containing 1 g of N-tert-butoxycarbonyl-trans-1,4-cyclohexanediamine, 632 mg of 3-pyridinecarboxylic acid, 1.07 g of 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide and 757 mg of 1-hydroxybenzotriazole was stirred at room temperature for 24 hours. To the reaction mixture was added an aqueous saturated sodium hydrogencarbonate solution and the resulting mixture was extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was washed with diethyl ether to obtain N-tert-butoxycarbonyl-trans-4-(3-pyridylcarbonylamino)cyclohexylamine. A mixture comprising 1.27 g of this compound and 13 ml of 15% hydrochloric acid-ethanol solution was stirred at 50° C. for 2 hours. After cooling, precipitates were filtered and washed with diethyl ether to obtain 1.12 g of trans-4-(3-pyridylcarbonylamino)cyclohexylamine dihydrochloride (Reference Example 10-2 in Table 11).

Quelle