Ethylene Glycol → 1-Phenylpyrrolidine

HRID 2179201Notes

Reaction equation

HRID 2179201 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-68fbe30eab974f23ad9215a770c608a7
Source dataset
uspto-grants-2015_06
Patent number
US09067955B2

Reaction notes

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