Morpholine → HCID 68467048, compound

HRID 506189Notes

Reaction equation

HRID 506189 reaction equation
Br[CH2:2][C:3]1[CH:8]=[C:7]([I:9])[CH:6]=[CH:5][N:4]=1.[NH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1>COCCOC.[I-].[Na+]>[I:9][C:7]1[CH:6]=[CH:5][N:4]=[C:3]([CH2:2][N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH:8]=1

Participants

5

Reactant 2

HCID 8083MorpholineHCID 59770941HCID 59770941, compound

Product 1

HCID 68467048HCID 68467048, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 5238Sodium IodideCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

2-(Bromomethyl)-4-iodopyridine (500 mg, 1.68 mmol) in 1,2-dimethoxyethane (15 ml) was treated with morpholine (1.00 g, 11.48 mmol) and sodium iodide (13 mg, 0.09 mmol) and the resulting solution was heated at 90° C. for 5 h. After cooled to room temperature, the reaction mixture was partitioned between dichloromethane and saturated aqueous sodium bicarbonate. The organic layer was dried over MgSO4 and concentrated to give 4-[(4-iodo-2-pyridinyl)methyl]morpholine as a brown solid (315 mg, 62% yield).

Workup

  1. temperatureAfter cooled to room temperature
  2. customthe reaction mixture was partitioned between dichloromethane and saturated aqueous sodium bicarbonate
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-65c6bec3b2ef4793b9f772119e6fd162
Source dataset
uspto-grants-2010_08
Patent number
US07781591B2

Reaction notes

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