Ethylene Glycol → 1-Phenylpyrrolidine

HRID 1243027Notes

Reaction equation

HRID 1243027 reaction equation
[O-]P([O-])([O-])=O.[K+].[K+].[K+].[NH:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1.I[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(O)CO>[Cu]I.CCCCCC.C(OCC)(=O)C.CC(O)C>[C:15]1([N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

8

Reactant 4

HCID 174Ethylene GlycolHCID 11575IodobenzeneHCID 31268PyrrolidineHCID 62657Potassium Phosphate, Tribasic

Product 1

HCID 777261-PhenylpyrrolidineYield 90.3%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 3776IsopropanolSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

The general procedure under argon or air was followed using copper(I) iodide (10 mg, 0.05 mmol or 2.0 mg, 0.01 mmol), K3PO4 (425 mg, 2.00 mmol), pyrrolidine (100 μL, 1.20 mmol), iodobenzene (112 μL, 1.00 mmol), ethylene glycol (111 μL, 2.00 mmol) and 2-propanol (1.0 mL). Column chromatography using a solvent mixture (hexane/ethyl acetate=20/1, Rf=0.4) afforded N-(phenyl)pyrrolidine (133 mg, 90% isolated yield) as colorless liquid. The spectral data (1H NMR) matched with the literature references and GC analysis indicated >95% purity. See Ishikawa, T.; Uedo, E.; Tani, R.; Saito, S. J. Org. Chem. 2001, 66, 186–191.

Sources & evidence

ORD record
ord-a4c2005f42c64a1ba5660986fecb902e
Source dataset
uspto-grants-2006_10
Patent number
US07115784B2

Reaction notes

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