Reaktion #46679

Reaktionsgleichung

2-(1-adamantyl)-N-propylethylamine

5-(4-pyridyl)valeric acid

N-Methylmorpholine

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

→

compound

Ausbeute 33.0%

5-(4-Pyridyl)valeric acid N-[2-(1-adamantyl)ethyl]-N-propylamide

Ausbeute 33.0%

Lösungsmittel

N,N-Dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGsuccessively, and the whole was stirred overnight
2. 2
   EinengenThe reaction mixture was concentrated under reduced pressure, ethyl acetate (20 ml)
3. 3
   workup.ADDITIONwas added to the residue
4. 4
   Waschenthe whole was washed with a saturated aqueous sodium hydrogencarbonate solution (20 ml) and saturated brine (5 ml) successively
5. 5
   TrocknenThe organic layer was dried over sodium sulfate, and ethyl acetate
6. 6
   Sonstigewas evaporated under reduced pressure
7. 7
   SonstigeThe residue was purified by basic silica gel column chromatography

Vorschrift

N,N-Dimethylformamide (8.4 ml) was added to a mixture of 2-(1-adamantyl)-N-propylethylamine (Intermediate No. 1-6, 0.37 g, 1.7 mmol) and 5-(4-pyridyl)valeric acid (Intermediate No. 5-1, 0.30 g, 1.7 mmol), and the whole was stirred at room temperature. N-Methylmorpholine (0.27 ml, 2.5 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.38 g, 2.0 mmol) were added thereto successively, and the whole was stirred overnight. The reaction mixture was concentrated under reduced pressure, ethyl acetate (20 ml) was added to the residue, and the whole was washed with a saturated aqueous sodium hydrogencarbonate solution (20 ml) and saturated brine (5 ml) successively. The organic layer was dried over sodium sulfate, and ethyl acetate was evaporated under reduced pressure. The residue was purified by basic silica gel column chromatography to give the target compound (0.21 g, 33%) as a colorless oily matter.

Quelle