Methylamine → 1-benzyl-N-methyl-5-oxopyrrolidine-3-carboxamide

HRID 464953Notes

Reaction equation

HRID 464953 reaction equation
[O:1]=[C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:5][CH:4]([C:14]([O:16]C)=O)[CH2:3]1.[CH3:18][NH2:19]>CO>[CH3:18][NH:19][C:14]([CH:4]1[CH2:3][C:2](=[O:1])[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:5]1)=[O:16]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 98909Methyl 1-benzyl-5-oxopyrrolidine-3-carboxylate

Product 1

HCID 134917941-benzyl-N-methyl-5-oxopyrrolidine-3-carboxamideYield 88.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 100 g (0.43 mole) of methyl 5-oxo-1-(phenylmethyl)-3-pyrrolidinecarboxylate [J. Org. Chem., 26, 1519 (1961)], 500 ml methanol and 100 g (3.2 mole) of methylamine was heated at 100° C. in a pressure reactor for 16 hours. The reaction mixture was cooled and the excess methylamine and methanol were removed under reduced pressure. The residue was taken up in dichloromethane and washed with 3×100 ml 1N sodium hydroxide. The organic layer was dried over magnesium sulfate and the solvent removed at reduced pressure to give 88.3 g of N-methyl-5-oxo-1-(phenylmethyl)-3-pyrrolidinecarboxamide as a white solid, mp 82.5°-83.0° C.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customthe excess methylamine and methanol were removed under reduced pressure
  3. washwashed with 3×100 ml 1N sodium hydroxide
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. customthe solvent removed at reduced pressure

Sources & evidence

ORD record
ord-82c616e578614ca98b38ef1760111d96
Source dataset
uspto-grants-1985_10
Patent number
US04550103

Reaction notes

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