Reacción #1483034

Ecuación de reacción

tert-butyl 2-aminoethylcarbamate

Et3N

nicotinic acid

oxalyl chloride

→

tert-butyl 2-(nicotinamido)ethylcarbamate

Rendimiento 74.0%

Disolventes

CH2Cl2

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.DISSOLUTIONhad dissolved
2. 2
   Otro(1 h)
3. 3
   OtroThe resulting reaction mixture
4. 4
   Temperaturawas warmed to room temperature
5. 5
   workup.STIRRINGstirred for 2 h
6. 6
   LavadoIt was then washed with brine
7. 7
   Secadodried over Na2SO4
8. 8
   Filtraciónfiltered
9. 9
   Concentraciónconcentrated under reduced pressure
10. 10
    OtroPurification by silica gel chromatography (CH2Cl2)

Procedimiento

In a typical run, nicotinic acid (2.0 g, 16.2 mmol) was taken up in CH2Cl2 (20 mL) along with oxalyl chloride (1.4 mL, 16.2 mmol). After a few drops of DMF were added, the reaction mixture was stirred at room temperature until all the solids had dissolved and all gas evolution had ceased (1 h). This freshly prepared solution of the acid chloride was added dropwise at 0° C. to a solution containing tert-butyl 2-aminoethylcarbamate (2.6 g, 16.2 mmol) and Et3N (3.4 mL, 24.2 mmol) in CH2Cl2 (200 mL). The resulting reaction mixture was warmed to room temperature and stirred for 2 h. It was then washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. Purification by silica gel chromatography (CH2Cl2) afforded tert-butyl 2-(nicotinamido)ethylcarbamate (3.1 g, 74%).

Fuente