Morpholine → 4-(4-Iodobenzyl)morpholine

HRID 1710410Notes

Reaction equation

HRID 1710410 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)morpholine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

1-Bromomethyl-4-iodobenzene (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-7c9cec820c2e4edf98ee7dde8aef9c68
Source dataset
uspto-grants-2010_09
Patent number
US07790717B2

Reaction notes

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