Ethylenediamine → Benzyl N-(2-aminoethyl)carbamate

HRID 1923983Notes

Reaction equation

HRID 1923983 reaction equation
[NH2:1][CH2:2][CH2:3][NH2:4].[C:5](C1CC(=O)N(O)C1=O)([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6]>C(Cl)(Cl)Cl.O>[NH2:1][CH2:2][CH2:3][NH:4][C:5](=[O:6])[O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 3301EthylenediamineHCID 22716645HCID 22716645, compound

Product 1

HCID 2794257Benzyl N-(2-aminoethyl)carbamateYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

To a solution of 2-aminoethylamine LVIII (150 mL; 2.25 mol) in chloroform (1.5 L), cooled to 0° C. was added a solution of carbobenzoxy N-hydroxysuccinimide (112.14 g; 0.45 mol) in water (0.5 L) with vigorously stirring for one hour. The solid was filtered and the solution was washed with brine (3×), once with water and dried over anhydrous MgSO4. The solvent was evaporated under reduced pressure and the residue was purified on a silica gel column (100:1→30:1 DCM:MeOH) to yield benzyl 2-aminoethylcarbamate LIX as a colorless viscous oil (350 g; 1.80 mol; 80% yield). 1H NMR (CDCl3) 2.79-2.83 (m, 2H), 3.21-3.28 (m, 2H), 5.10 (s, 2H), 5.19 (brs, 1H), 7.29-7.34 (m, 1H), 7.35-7.38 (m, 4H); ESIMS found for C10H14N2O2 m/z 195.2 (M+H).

Workup

  1. filtrationThe solid was filtered
  2. washthe solution was washed with brine (3×), once with water
  3. dry with materialdried over anhydrous MgSO4
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified on a silica gel column (100:1→30:1 DCM:MeOH)

Sources & evidence

ORD record
ord-78f458d1a13443b4ba484f2bf71c2d78
Source dataset
uspto-grants-2012_05
Patent number
US08178490B2

Reaction notes

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