Pyrrolidine → 1-[(3-Nitrophenyl)methyl]pyrrolidine

HRID 1633594

반응식

HRID 1633594 반응식
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH2:7]Br)([O-:3])=[O:2].[NH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1>C1COCC1>[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH2:7][N:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1)([O-:3])=[O:2]

참가 물질

4

반응물 2

HCID 31268PyrrolidineHCID 77568Benzene, 1-(bromomethyl)-3-nitro-

생성물 1

HCID 7828801-[(3-Nitrophenyl)methyl]pyrrolidine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of 3-nitrobenzylbromide (3 g, 13.9 mmol) in anhydrous THF (30 ml) was added a solution of pyrrolidine (2.3 ml, 27.8 mmol) in anhydrous THF (10 ml) dropwise with stirring. Following the addition the mixture was stirred at ambient temperature overnight. The reaction mixture was filtered. The filter cake was washed with a small volume of anhydrous THF and the filtrate was concentrated to leave the intermediate 1-(3-nitrobenzyl)pyrrolidine as an oil. This oil was dissolved in methanol (50 ml) and three equivalents of both ammonium chloride and sodium sulfide nonahydrate were added. The mixture was heated to reflux for 2 hours. After cooling the mixture was filtered. The filtercake was washed with methanol and the filtrate was concentrated under reduced pressure. The residue was dissolved in ethyl acetate and dried over sodium sulfate. Filtration and evaporation of solvent left 2i quantitatively as yellow crystals.

후처리

  1. additionthe addition the mixture
  2. stirringwas stirred at ambient temperature overnight
  3. filtrationThe reaction mixture was filtered
  4. washThe filter cake was washed with a small volume of anhydrous THF
  5. concentrationthe filtrate was concentrated

출처 및 근거

ORD 기록
ord-f589340123f042b6836598ac09fedd47
출처 데이터셋
uspto-grants-2003_01
특허 번호
US06503925B1

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