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

HRID 364030

Reaktionsgleichung

Reaktionsgleichung von HRID 364030
[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]

Komponenten

4

Edukt 2

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

Produkt 1

HCID 134917941-benzyl-N-methyl-5-oxopyrrolidine-3-carboxamideAusbeute 88,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

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 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.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled
  2. customthe ammonia 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

Quellen und Nachweise

ORD-Eintrag
ord-4b7e98998c2043f1ab9442150b84b674
Quelldatensatz
uspto-grants-1986_08
Patentnummer
US04604401

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