Reaction #1483039

Reaction equation

tert-Butyl 2-((2-aminoethyl)(methyl)amino)ethylcarbamate

nicotinic acid

EDCI

→

tert-butyl 2-(methyl(2-(nicotinamido)ethyl)amino)ethylcarbamate

Yield 30.3%

Solvents

CH3CN

EtOAc

Conditions

Workup

1. 1
   OtherThe resulting reaction mixture
2. 2
   WashThe organic layer was washed with saturated aqueous NaHCO3, brine
3. 3
   Dryingdried over Na2SO4
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated under reduced pressure
6. 6
   OtherThe resulting residue was purified by silica gel chromatography (5% MeOH—CH2Cl2)

Procedure

tert-Butyl 2-((2-aminoethyl)(methyl)amino)ethylcarbamate (400 mg, 1.84 mmol) was taken up in CH3CN (10 mL) along with nicotinic acid (227 mg, 1.84 mmol) and EDCI (353 mg, 2.02 mmol). The resulting reaction mixture was stirred at room temperature for 18 h and then diluted with EtOAc. The organic layer was washed with saturated aqueous NaHCO3, brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (5% MeOH—CH2Cl2) to afford tert-butyl 2-(methyl(2-(nicotinamido)ethyl)amino)ethylcarbamate (180 mg, 30%). MS calculated for C16H26N4O3: 322.2. found: [M+H]+ 323.

Source