Hydrochloric Acid → 1-Amino-4-(3-methoxy-phenyl)-pyrrolidin-2-one

HRID 8203Notes

Reaction equation

HRID 8203 reaction equation
Cl.C(=[N:15][N:16]1[CH2:20][CH:19]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[CH:22]=2)[CH2:18][C:17]1=[O:29])(C1C=CC=CC=1)C1C=CC=CC=1>O>[NH2:15][N:16]1[CH2:20][CH:19]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[CH:22]=2)[CH2:18][C:17]1=[O:29]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 219926151-(Benzhydrylidene-amino)-4-(3-methoxy-phenyl)-pyrrolidin-2-one

Product 1

HCID 219926971-Amino-4-(3-methoxy-phenyl)-pyrrolidin-2-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Concentrated hydrochloric acid (0.35 mL) is added to a suspension of 1-(benzhydrylidene-amino)-4-(3-methoxy-phenyl)-pyrrolidin-2-one, (0.8 g, 2.16 mmol) in water (17 mL) and refluxed for one hour. The mixture is concentrated in vacuo and water azeotroped away using ethanol and toluene. The residue is dissolved in methanol (5 mL) and loaded on SCX resin (5 g). The resin is washed with methanol and 2 M solution of ammonia in methanol. Appropriate fractions are concentrated to yield the title compound, 402 mg (92%), as a white crystalline solid.

Workup

  1. temperaturerefluxed for one hour
  2. concentrationThe mixture is concentrated in vacuo and water
  3. customazeotroped away using ethanol and toluene
  4. dissolutionThe residue is dissolved in methanol (5 mL)
  5. washThe resin is washed with methanol and 2 M solution of ammonia in methanol
  6. concentrationAppropriate fractions are concentrated

Sources & evidence

ORD record
ord-ea0419dad2e9469f94ef59108d4767eb
Source dataset
uspto-grants-2006_08
Patent number
US07087626B2

Reaction notes

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