N-Methylethylenediamine → N-Methyl-N,N'-dibenzyloxycarbonyl-1,2-diaminoethane

HRID 64600Notes

Reaction equation

HRID 64600 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][NH2:5].C(N([CH2:11][CH3:12])CC)C.Cl[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15]>C(Cl)(Cl)Cl>[CH3:1][N:2]([C:14]([O:16][CH2:17][C:12]1[CH:11]=[CH:20][CH:19]=[CH:18][CH:23]=1)=[O:15])[CH2:3][CH2:4][NH:5][C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15]

Participants

5

Reactant 3

HCID 8014N-MethylethylenediamineHCID 8471TriethylamineHCID 10387Benzyl chloroformate

Product 1

HCID 20236398N-Methyl-N,N'-dibenzyloxycarbonyl-1,2-diaminoethaneYield 86.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred solution of N-Methyl-1,2 diaminoethane (7.4 gm) and triethylamine (20.2 gm) in chloroform (50 ml) at 0° was added dropwise over 30 minutes benzyl chloroformate (34.1 gm). The mixture was then left to warm to room temperature over one hour. The organic solution was then washed with water, citric acid solution, sodium bicarbonate solution and finally water again. The chloroform solution was dried over magnesium sulphate and evaporated to give a yellow oil (29.6 g).

Workup

  1. waitThe mixture was then left
  2. washThe organic solution was then washed with water, citric acid solution, sodium bicarbonate solution and finally water again
  3. dry with materialThe chloroform solution was dried over magnesium sulphate
  4. customevaporated

Sources & evidence

ORD record
ord-fc4ee2f951a3402093aaa701a22ec91b
Source dataset
uspto-grants-1986_09
Patent number
US04609495

Reaction notes

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