Acetic Acid → HCID 66873035, compound

HRID 254411Notes

Reaction equation

HRID 254411 reaction equation
ClCCl.[CH2:4]([N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)[CH3:5].C(O)(=O)C.[I:22]I>FC(F)(F)S([O-])(=O)=O.[Ag+].C(OCC)(=O)C>[CH2:4]([N:6]1[CH2:7][CH2:8][CH:9]([C:12]2[CH:17]=[CH:16][C:15]([I:22])=[CH:14][CH:13]=2)[CH2:10][CH2:11]1)[CH3:5]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 807IodineHCID 6344DichloromethaneHCID 21600148HCID 21600148, compound2×

Product 1

HCID 66873035HCID 66873035, compound

Reagents, catalysts & solvents 2

HCID 76223Silver(I) trifluoromethanesulfonateCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A dichloromethane (36 mL) mixture of 1-ethyl-4-phenylpiperidine (1.37 g, 7.23 mmol), acetic acid (500 μL), silver trifluoromethanesulfonate (3.72 g), and iodine (3.67 g) was stirred overnight. Ethyl acetate was added, then the insoluble matter was removed by filtration. The obtained filtrate was washed with ammonia water, aqueous sodium thiosulfate solution and saturated saline. After dried with anhydrous magnesium sulfate, this was concentrated and purified by flash column chromatography (FPNH, hexane:ethyl acetate=1 to 9:1) to obtain a mixture of the entitled compound and 1-ethyl-4-phenylpiperidine (2.52 g).

Workup

  1. customthe insoluble matter was removed by filtration
  2. washThe obtained filtrate was washed with ammonia water, aqueous sodium thiosulfate solution and saturated saline
  3. dry with materialAfter dried with anhydrous magnesium sulfate
  4. concentrationthis was concentrated
  5. custompurified by flash column chromatography (FPNH, hexane:ethyl acetate=1 to 9:1)
  6. customto obtain

Sources & evidence

ORD record
ord-3b4711579f664af1a79e0476a1aff44e
Source dataset
uspto-grants-2011_01
Patent number
US07875633B2

Reaction notes

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