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

HRID 364032

반응식

HRID 364032 반응식
[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]

참가 물질

4

반응물 2

HCID 6341EthylamineHCID 98909Methyl 1-benzyl-5-oxopyrrolidine-3-carboxylate

생성물 1

HCID 13491793N-ethyl-5-oxo-1-(phenylmethyl)-3-pyrrolidinecarboxamide수율 49.4%

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
100 °C

실험 절차

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.

후처리

  1. temperatureThe reaction mixture was cooled
  2. customthe excess ethylamine and methanol were removed under reduced pressure
  3. washwashed with 3×150 ml 1N sodium hydroxide
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. customthe solvent removed at reduced pressure

출처 및 근거

ORD 기록
ord-3f7bae9d6f1e42a2a0272f57ddd383b6
출처 데이터셋
uspto-grants-1986_08
특허 번호
US04604401

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