Morpholine → 4-(4-Iodobenzyl)morpholine

HRID 1724077Notes

Reaction equation

HRID 1724077 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([I:9])=[CH:5][CH:4]=1.[NH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1>C(OCC)(=O)C>[I:9][C:6]1[CH:7]=[CH:8][C:3]([CH2:2][N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[CH:4][CH:5]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 9542584-Iodobenzyl bromide

Product 1

HCID 27955004-(4-Iodobenzyl)morpholineYield 92%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

1-Bromomethyl-4-iodo-benzene (320 mg, 1.08 mmol) and morpholine (1 mL, 11.47 mmol) were combined. The reaction mixture was heated at 70° C. for 4 hours and then diluted with ethyl acetate. The resulting mixture was filtered and the filtrate was concentrated and dried. The residue was then dissolved in dichloromethane (10 mL), washed with water (4 mL), washed with brine (4 mL), dried over sodium sulfate and concentrated to give the product as an off-white solid (300 mg, 92%). 1H NMR (300 MHz, CDCl3): δ 7.64 (d, 2H), 7.09 (d, 2H), 3.7 (t, 4H), 3.43 (s, 2H), 2.43 (t, 4H).

Workup

  1. filtrationThe resulting mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customdried
  4. dissolutionThe residue was then dissolved in dichloromethane (10 mL)
  5. washwashed with water (4 mL)
  6. washwashed with brine (4 mL)
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-1bfb04a0691345788fdb9d6768264b0e
Source dataset
uspto-grants-2009_02
Patent number
US07485722B2

Reaction notes

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