Methylamine → 1-benzyl-N-methyl-5-oxopyrrolidine-3-carboxamide
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
Product 1
Reagents, catalysts & solvents 1
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 ammonia and methanol were removed under pressure. The residue was taken up in dichloromethane and washed 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
- temperatureThe reaction mixture was cooled
- customthe ammonia and methanol were removed under pressure
- washwashed 3×100 ml 1N sodium hydroxide
- dry with materialThe organic layer was dried over magnesium sulfate
- customthe solvent removed at reduced pressure
Sources & evidence
- ORD record
- ord-2acb4fa0ad09416597e97e9875cc9f01
- Source dataset
- uspto-grants-1992_03
- Patent number
- US05097032
Reaction notes
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