Potassium Iodide → 1-Benzhydryl-3-iodoazetidine

HRID 634023Notes

Reaction equation

HRID 634023 reaction equation
[I-:1].[K+].CS(O[CH:8]1[CH2:11][N:10]([CH:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:9]1)(=O)=O.C(OCC)(=O)C>O.COCCOC>[CH:12]([N:10]1[CH2:11][CH:8]([I:1])[CH2:9]1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 4875Potassium IodideHCID 8857Ethyl AcetateHCID 27587161-(Diphenylmethyl)azetidin-3-yl methanesulfonate

Product 1

HCID 73306101-Benzhydryl-3-iodoazetidine

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Procedure

Potassium iodide (530 mg, 3.14 mmol) was added to a solution of 1-benzhydrylazetidin-3-yl methanesulfonate (500 mg, 1.57 mmol) in a mixture of water (2.5 mL) and 1,2-dimethoxyethane (2.5 mL) at room temperature. The reaction mixture was then heated up to reflux and stirred for 3 hours. After cooling down to room temperature, the reaction mixture was diluted by addition of water (50 mL) and ethyl acetate (50 mL). The aqueous phase was separated and extracted with ethyl acetate (2×70 mL). The combined organic phases were washed with a saturated solution of sodium chloride (40 mL), dried over sodium sulfate, filtered and concentrated to dryness. The title compound was obtained as a yellow solid (550 mg, 100%).

Workup

  1. temperatureThe reaction mixture was then heated up
  2. temperatureto reflux
  3. customThe aqueous phase was separated
  4. extractionextracted with ethyl acetate (2×70 mL)
  5. washThe combined organic phases were washed with a saturated solution of sodium chloride (40 mL)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-bf323638039a4e34ab2a098356fa14dd
Source dataset
uspto-grants-2016_04
Patent number
US09321769B2

Reaction notes

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