Sodium Iodide → 1-[2-(3-Methyl-2-nitrophenoxy)-ethyl]-pyrrolidine

HRID 6949

반응식

HRID 6949 반응식
C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].[CH3:9][C:10]1[C:11]([N+:17]([O-:19])=[O:18])=[C:12]([OH:16])[CH:13]=[CH:14][CH:15]=1.Cl.Cl[CH2:22][CH2:23][N:24]1[CH2:28][CH2:27][CH2:26][CH2:25]1>>[CH3:9][C:10]1[C:11]([N+:17]([O-:19])=[O:18])=[C:12]([CH:13]=[CH:14][CH:15]=1)[O:16][CH2:22][CH2:23][N:24]1[CH2:28][CH2:27][CH2:26][CH2:25]1

참가 물질

5

반응물 4

HCID 5238Sodium IodideHCID 11430Potassium Carbonate2회HCID 210263-Methyl-2-nitrophenolHCID 816681-(2-Chloroethyl)pyrrolidine hydrochloride2회

생성물 1

HCID 116012601-[2-(3-Methyl-2-nitrophenoxy)-ethyl]-pyrrolidine수율 69%

실험 절차

Potassium carbonate (34.9 g., 252 mmol) and sodium iodide (1.0 g., 6.5 mmol) were added to a solution of 3-methyl-2-nitrophenol (10 g., 65.3 mmol). With stirring, 1-(2-chloroethyl)-pyrrolidine hydrochloride (16.65 g., 98 mmol) was added portion-wise to the solution. The reaction mixture was refluxed for 15 hours, at which time 1-(2-chloroethyl)-pyrrolidine hydrochloride (8.5 g., 50 mmol) and potassium carbonate (18 g., 130 mmol) were added. After an additional hour of reflux, the reaction mixture was allowed to cool to room temperature and was washed with sequentially with water (1×100 mL) and brine (1×100 mL.) The combined organic fractions spontaneously crystallized, and the solid was purified by flash chromatography (5% MeOH in CH2Cl2) to give 1-[2-(3-Methyl-2-nitrophenoxy)-ethyl]-pyrrolidine (10.291 g., 69%). MS: 251 (M+H)+

후처리

  1. additionwere added
  2. temperatureAfter an additional hour of reflux
  3. washwas washed with sequentially with water (1×100 mL) and brine (1×100 mL.) The combined organic fractions
  4. customspontaneously crystallized
  5. customthe solid was purified by flash chromatography (5% MeOH in CH2Cl2)

출처 및 근거

ORD 기록
ord-053aef3bb4e14e958a06b1ca6a830675
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07084169B2

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