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

HRID 6949

Reaction equation

HRID 6949 reaction equation
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

Participants

5

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium Carbonate2×HCID 210263-Methyl-2-nitrophenolHCID 816681-(2-Chloroethyl)pyrrolidine hydrochloride2×

Product 1

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

Procedure

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)+

Workup

  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)

Sources & evidence

ORD record
ord-053aef3bb4e14e958a06b1ca6a830675
Source dataset
uspto-grants-2006_08
Patent number
US07084169B2

Linked notes

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