Ethylenediamine → Benzyl N-(2-aminoethyl)carbamate

Ethylenediamine (1.0 g, 16.7 mmol) is dissolved in water (3.0 mL) containing bromoaresal green as an indicator. Methane sulfonic acid (2.8 g, 31 mmol) in water (3.0 ml) was added until a blue to pale yellow color transition is just achieved. The solution was diluted with ethanol (8.0 mL) and vigorously stirred. To the mixture was added the solution of Cbz-Cl (2.8 g, 16.7 mmol) in dimethoxyethane (4 mL) and 50% w/v aqueous AcOK (10 mL) at 20° C. simultaneously to maintain the pale yellow-green color of the indicator. After the additions are complete the mixture was stirred (RT, 1 h) and concentrated at low temperature under vacuum to removed the volatiles. The residue was shaken with water (20 mL) and filtered. The filtrate was then washed with toluene (3×50 mL), basified with excess 40% aqueous NaOH and extracted with toluene (3×50 mL). The organic layer was washed with brine (50 mL), dried over Na2SO4 and evaporated to give benzyl 2-aminoethylcarbamate as an oil (1.65 g, 51%). Mass calculated for C10H14N2O2=194.23. found: [M−H]+=193.3.

1. additioncontaining bromoaresal green as an indicator
2. customat 20° C.
3. temperatureto maintain the pale yellow-green color of the indicator
4. stirringwas stirred (RT, 1 h)
5. concentrationconcentrated at low temperature under vacuum
6. customto removed the volatiles
7. stirringThe residue was shaken with water (20 mL)
8. filtrationfiltered
9. washThe filtrate was then washed with toluene (3×50 mL)
10. extractionextracted with toluene (3×50 mL)
11. washThe organic layer was washed with brine (50 mL)
12. dry with materialdried over Na2SO4
13. customevaporated

ORD record

ord-9fd090db599c400ca4c25a164356f5b9

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09272984B2