Ethylene Glycol → 1-Phenylpiperidine

HRID 984616Notes

Reaction equation

HRID 984616 reaction equation
[O-]P([O-])([O-])=O.[K+].[K+].[K+].[NH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.I[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(O)CO>[Cu]I.CCCCCC.C(OCC)(=O)C.CC(O)C>[C:16]1([N:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

8

Reactant 4

HCID 174Ethylene GlycolHCID 8082PiperidineHCID 11575IodobenzeneHCID 62657Potassium Phosphate, Tribasic

Product 1

HCID 200381-PhenylpiperidineYield 80%

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 was followed using copper(I) iodide (10 mg, 0.05 mmol), K3PO4 (425 mg, 2.00 mmol), piperidine (119 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)piperidine (129 mg, 80% isolated yield) as colorless liquid. The spectral data (1H NMR) matched with the literature references and GC analysis indicated >95% purity. See Beller, M.; Breindl, C.; Riermeier, T. H.; Tillack, A. J. Org. Chem. 2001, 66, 1403-1412; and Li, G. Y. Angew. Chem., Int. Ed. 2001, 40, 1513-1516.

Sources & evidence

ORD record
ord-cab740070a0f465a9aa8e5505b795429
Source dataset
uspto-grants-2005_03
Patent number
US06867298B2

Reaction notes

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