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

HRID 464618Notes

Reaction equation

HRID 464618 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-d02c5d38b2684ab5809f153648e76a7d
Source dataset
uspto-grants-1985_10
Patent number
US04548815

Reaction notes

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