Ammonia → 1-Benzyl-5-oxopyrrolidine-3-carboxamide

HRID 1276359Notes

Reaction equation

HRID 1276359 reaction equation
[CH2:1]([N:8]1[C:12](=[O:13])[CH2:11][CH:10]([C:14]([O:16]C)=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH3:18].CO>>[CH2:1]([N:8]1[C:12](=[O:13])[CH2:11][CH:10]([C:14]([NH2:18])=[O:16])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 98909Methyl 1-benzyl-5-oxopyrrolidine-3-carboxylate

Product 1

HCID 52217541-Benzyl-5-oxopyrrolidine-3-carboxamide

Conditions

Temperature
50 °C

Procedure

Methyl 1-benzyl-5-oxo-3-pyrrolidinecarboxylate (50 g, 0.21 mol) was stirred in a solution of ammonia in methanol (7 M, 400 mL, 2.8 mol). After 2 days, the solution was concentrated with heating (50° C.) to about 300 mL at which point all solids remained dissolved. The reaction was then allowed to cool down and the resulting solid was filtered, washed with ether and dried to give 1-benzyl-5-oxo-pyrrolidine-3-carboxylic acid amide as colorless crystals (40 g).

Workup

  1. concentrationthe solution was concentrated
  2. dissolutionremained dissolved
  3. temperatureto cool down
  4. filtrationthe resulting solid was filtered
  5. washwashed with ether
  6. customdried

Sources & evidence

ORD record
ord-bab8c93abf62418c89aac35e4e2a1027
Source dataset
uspto-grants-2000_12
Patent number
US06166015

Reaction notes

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