Benzophenone imine → 3-(Benzhydrylidene-amino)-1-methyl-pyrrolidin-2-one

HRID 626873Notes

Reaction equation

HRID 626873 reaction equation
[C:1](=[NH:14])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N[CH:16]1[CH2:20][CH2:19][N:18]([CH3:21])[C:17]1=[O:22]>ClCCCl>[C:1](=[N:14][CH:16]1[CH2:20][CH2:19][N:18]([CH3:21])[C:17]1=[O:22])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 136809Benzophenone imineHCID 457911333-Amino-1-methylpyrrolidin-2-one

Product 1

HCID 896489983-(Benzhydrylidene-amino)-1-methyl-pyrrolidin-2-one

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Benzophenone imine [CAS: 1013-88-3] (16.67 g, 91.98 mmol) was added dropwise to a solution of 3-amino-1-methylpyrrolidine-2-one [CAS 119329-48-5] (10 g, 87.60 mmol) in DCE (100 mL) under N2 and the reaction was heated at reflux for 18 hours. The solvent was evaporated to afford an amber oil. This was purified using flash silica in a large sinter funnel, eluting with 4:1 to 3:7 i-hexane:EtOAc. An incomplete separation was achieved. 3-(Benzhydrylidene-amino)-1-methyl-pyrrolidin-2-one (D1) was isolated (25 g) with approximately 11% of an impurity present, but was used in the next step without further purification;

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 18 hours
  3. customThe solvent was evaporated
  4. customto afford an amber oil
  5. customThis was purified
  6. washeluting with 4:1 to 3:7 i-hexane
  7. customAn incomplete separation

Sources & evidence

ORD record
ord-47c8073d19b94c70913f6f2748c967cc
Source dataset
uspto-grants-2016_04
Patent number
US09309254B2

Reaction notes

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