Water → HCID 46208245, compound

HRID 2041891Notes

Reaction equation

HRID 2041891 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1([O:13][CH3:14])[CH2:12][NH:11][CH2:10]1.C(=O)([O-])[O-].[K+].[K+].I[CH2:22][CH3:23].O>C(#N)C.C(OCC)(=O)C>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1([O:13][CH3:14])[CH2:12][N:11]([CH2:22][CH3:23])[CH2:10]1

Participants

7

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 46208244HCID 46208244, compound

Product 1

HCID 46208245HCID 46208245, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-(2,3-difluorophenyl)-3-methoxyazetidine (0.75 g, 4.05 mmol), potassium carbonate (0.99 g, 8.1 mmol) and iodoethane (0.388 ml, 4.05 mmol) in acetonitrile (25 ml) was stirred at ambient temperature for 1 h. Water (50 mL) and ethyl acetate (50 mL) was added, the organic phase was collected and the aqueous phase was extracted with ethyl acetate (2×50 ml). The combined organic phase was dried (Na2SO4), filtered and evaporated to dryness. The crude product was purified by flash column chromatography on silica gel (ethyl acetate/methanol 1:1) to give the title compound (0.58 g, 63%). The amine was converted to the oxalic acid salt and recrystallized from ethanol/diethyl ether/diisopropyl ether: M.p. 147-148° C. MS m/z (relative intensity, 70 eV) 227 (M+, 4), 170 (66), 169 (bp), 140 (63), 127 (39).

Workup

  1. customthe organic phase was collected
  2. extractionthe aqueous phase was extracted with ethyl acetate (2×50 ml)
  3. dry with materialThe combined organic phase was dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe crude product was purified by flash column chromatography on silica gel (ethyl acetate/methanol 1:1)

Sources & evidence

ORD record
ord-65ac100bbd27427da95d1dc01eaa81db
Source dataset
uspto-grants-2013_11
Patent number
US08586572B2

Reaction notes

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