Reacción #11559

Ecuación de reacción

2-(1-adamantyl)-N-propylethylamine

5-(4-pyridyl)valeric acid

N-Methylmorpholine

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

→

titled compound

Rendimiento 33.0%

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

Rendimiento 33.0%

Disolventes

N,N-Dimethylformamide

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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 then 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.38 g, 2.0 mmol) were added thereto, 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 0.21 g (33%) of the titled compound as a colorless oily matter.

Fuente