Benzylamine → 1-[(Benzylcarbamoyl)oxy]pyrrolidine-2,5-dione

HRID 744899Notes

Reaction equation

HRID 744899 reaction equation
C1C(=O)N(O[C:9]([O:11][N:12]2[C:17](=[O:18])[CH2:16][CH2:15][C:13]2=[O:14])=[O:10])C(=O)C1.[CH2:19]([NH2:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(#N)C>[CH2:19]([NH:26][C:9](=[O:10])[O:11][N:12]1[C:13](=[O:14])[CH2:15][CH2:16][C:17]1=[O:18])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 676246Di(succinimido) carbonate

Product 1

HCID 131119021-[(Benzylcarbamoyl)oxy]pyrrolidine-2,5-dioneYield 76.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

18.4 g of N,N'-disuccinimidyl carbonate are added in small portions at 5° C. within 5 minutes to a solution of 6.4 g of benzylamine in 150 ml of acetonitrile. The reaction mixture is stirred at room temperature and then evaporated. The residue is taken up in ethyl acetate and washed with water. The organic phase is dried, concentrated and the residue is recrystallized from methylene chlorideohexane. 11.3 g of colourless 2,5-dioxo-pyrrolidin-1-yl benzylcarbamate, MS (FAB): 133 (M- HO-Succ), are isolated.

Workup

  1. customevaporated
  2. washwashed with water
  3. customThe organic phase is dried
  4. concentrationconcentrated
  5. customthe residue is recrystallized from methylene chlorideohexane

Sources & evidence

ORD record
ord-b9bf4828c6d94554ac084721824d2361
Source dataset
uspto-grants-1996_09
Patent number
US05559232

Reaction notes

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