Ethylamine → N-ethyl-5-oxo-1-(phenylmethyl)-3-pyrrolidinecarboxamide
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.[CH2:18]([NH2:20])[CH3:19]>CO>[CH2:18]([NH:20][C:14]([CH:4]1[CH2:3][C:2](=[O:1])[N:6]([CH2:7][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:5]1)=[O:16])[CH3:19]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
A mixture of 200 g (0.86 mole) of methyl 5-oxo-1-(phenylmethyl)-3-pyrrolidinecarboxylate [J. Org. Chem., 26, 1519 (1961)], 1000 ml methanol and 200 g (4.4 mole) of ethylamine was heated at 100° C. in a pressure reactor for 17.2 hours. The reaction mixture was cooled and the excess ethylamine and methanol were removed under reduced pressure. The residue was taken up in dichloromethane and washed with 3×150 ml 1N sodium hydroxide. The organic layer was dried over magnesium sulfate and the solvent removed at reduced pressure to give 104.6 g of N-ethyl-5-oxo-1-(phenylmethyl)- 3-pyrrolidinecarboxamide as a white solid, mp 97°-99° C.
Workup
- temperatureThe reaction mixture was cooled
- customthe excess ethylamine and methanol were removed under reduced pressure
- washwashed with 3×150 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-d6ddcce16e534c209b33cb3d08e833a5
- Source dataset
- uspto-grants-1985_10
- Patent number
- US04550103
Reaction notes
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