Water → benzyl 2-(methylamino)ethylcarbamate

HRID 2066388Notes

Reaction equation

HRID 2066388 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][NH2:5].[C:6](N1C(=O)CCC1=O)([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7].O.C(Cl)(Cl)Cl>O1CCOCC1>[CH3:1][NH:2][CH2:3][CH2:4][NH:5][C:6](=[O:7])[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6212ChloroformHCID 8014N-MethylethylenediamineHCID 3826287Benzyl 2,5-dioxopyrrolidine-1-carboxylate

Product 1

HCID 10822258benzyl 2-(methylamino)ethylcarbamateYield 4.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

N-Methylethylenediamine (2.0 g) was dissolved in dioxane (20 ml), the solution was added with N-carbobenzoxysuccinimide (8.07 g), and the mixture was stirred at room temperature for 4 days. The reaction mixture was added with distilled water and chloroform, the layers were separated, and the organic layer was dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1 to 2:1), and then purified again by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia=30:1:0.1) to obtain the title compound (243 mg).

Workup

  1. customthe layers were separated
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1 to 2:1)
  6. custompurified again by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia=30:1:0.1)

Sources & evidence

ORD record
ord-8f6ebaae1c2e436fb4d6c409df3c04a3
Source dataset
uspto-grants-2012_10
Patent number
US08293715B2

Reaction notes

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