Morpholine → 4-Phenylmorpholine

HRID 641900

Reaction equation

HRID 641900 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1.N1CCC[C@H]1C(O)=O>[Cu]I.CS(C)=O>[C:2]1([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8083MorpholineHCID 11575IodobenzeneHCID 145742L-Proline

Product 1

HCID 623394-PhenylmorpholineYield 44.4%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

1-iodobenzene (28.12 g, 137.84 mmol) was added to morpholine (12.0 g, 137.93 mmol). L-Proline (3.12 g, 27.13 mmol) was then added, followed by the addition of CuI (2.6 g, 13.68 mmol) and DMSO (120 mL). The resulting solution was stirred at 90° C. for 4 hours, and then the reaction mixture was then quenched by the addition of 300 mL of iced water. The resulting solution was extracted using dichloromethane (2×200 mL), and the organic layers combined, dried (Na2SO4) and concentrated. The residue was purified by column chromatography using a petroleum ether solvent system. The collected fractions were combined and concentrated to give 10 g (42%) of 4-phenylmorpholine as a white solid.

Workup

  1. customthe reaction mixture was then quenched by the addition of 300 mL of iced water
  2. extractionThe resulting solution was extracted
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4164fd1b61e74a6d9f80aaaaffc40ee9
Source dataset
uspto-grants-2010_04
Patent number
US07696229B2

Linked notes

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