Reaction #1483034

Reaction equation

tert-butyl 2-aminoethylcarbamate

Et3N

nicotinic acid

oxalyl chloride

→

tert-butyl 2-(nicotinamido)ethylcarbamate

Yield 74.0%

Solvents

CH2Cl2

CH2Cl2

Conditions

Workup

1. 1
   workup.DISSOLUTIONhad dissolved
2. 2
   Other(1 h)
3. 3
   OtherThe resulting reaction mixture
4. 4
   Temperaturewas warmed to room temperature
5. 5
   workup.STIRRINGstirred for 2 h
6. 6
   WashIt was then washed with brine
7. 7
   Dryingdried over Na2SO4
8. 8
   Filtrationfiltered
9. 9
   Concentrationconcentrated under reduced pressure
10. 10
    OtherPurification by silica gel chromatography (CH2Cl2)

Procedure

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%).

Source