N,N-Dimethylaniline → Benzyl 4-(2-oxo-1-pyrrolidinyl)phenylcarbamate

HRID 499733

Reaction equation

HRID 499733 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]2[CH2:23][CH2:22][CH2:21][C:20]2=[O:24])=[CH:15][CH:14]=1.CN(C)C1C=CC=CC=1.C(OCC)(=O)C>O1CCCC1>[O:24]=[C:20]1[CH2:21][CH2:22][CH2:23][N:19]1[C:16]1[CH:17]=[CH:18][C:13]([NH:12][C:2](=[O:3])[O:4][CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 949N,N-DimethylanilineHCID 8857Ethyl AcetateHCID 10387Benzyl chloroformateHCID 676146Pyrrolidinone, (4-aminophenyl)-

Product 1

HCID 7686496Benzyl 4-(2-oxo-1-pyrrolidinyl)phenylcarbamateYield 73.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

4.27 g (25.03 mmol) of benzyl chloroformate are slowly added to 4 g (22.7 mmol) of 1-(4-aminophenyl)pyrrolidin-2-one and 3.6 ml (28.4 mmol) of N,N-dimethylaniline in 107 ml of tetrahydrofuran at −20° C. The mixture is stirred at −20° C. for 30 minutes and then allowed to reach room temperature. 0.5 l of ethyl acetate is added, and the organic phase is washed with 0.5 l of saturated NaCl solution. The removed organic phase is dried with MgSO4, and the solvent is evaporated in vacuo. The residue is triturated with diethyl ether and filtered off with suction. 5.2 g (73.8% of theory) of benzyl 4-(2-oxo-1-pyrrolidinyl)phenylcarbamate are obtained as pale beige crystals with a melting point of 174° C.

Workup

  1. customto reach room temperature
  2. washthe organic phase is washed with 0.5 l of saturated NaCl solution
  3. dry with materialThe removed organic phase is dried with MgSO4
  4. customthe solvent is evaporated in vacuo
  5. customThe residue is triturated with diethyl ether
  6. filtrationfiltered off with suction

Sources & evidence

ORD record
ord-b678ad7d47524d1ab57465d1e6ea7d61
Source dataset
uspto-grants-2010_08
Patent number
US07767702B2

Linked notes

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