Ethylamine → N-ethyl-5-oxo-1-(phenylmethyl)-3-pyrrolidinecarboxamide

HRID 364032

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

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-3f7bae9d6f1e42a2a0272f57ddd383b6
Source dataset: uspto-grants-1986_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04604401

Linked notes

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