Iodine → 1-(4-Iodophenyl)piperazine

HRID 865332

Reaction equation

HRID 865332 reaction equation
[I:1]I.[C:3]1([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>C(O)(=O)C.C([O-])(=O)C1C=CC=CC=1.[Ag+]>[I:1][C:6]1[CH:7]=[CH:8][C:3]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:4][CH:5]=1

Participants

5

Reactant 2

HCID 807IodineHCID 70961-Phenylpiperazine

Product 1

HCID 41478451-(4-Iodophenyl)piperazineYield 11.3%

Reagents, catalysts & solvents 2

HCID 164649Silver benzoateCatalystHCID 176Acetic AcidSolvent

Procedure

Over a period of 15 minutes samples of iodine (8.62 grams, 0.034 mol) and silver benzoate (7.78 grams, 0.034mol) were added in portions to a magnetically stirred solution of 5 grams of 1-phenylpiperazine in 80 mL acetic acid. The mixture stirred for Ihour. The solvent was evaporated and the residue partioned between 150 mL diethyl ether and 150 mL 2N sodium hydroxide. The organic layer was washed with 100 mL water, 100 mL brine, then dried over potassium carbonate and concentrated in vacuo to yield 1.0 gram (11%) of 1-(4-iodophenyl)-piperzine (110°-115° C.). The material obtained wasused without further purification. 1H NMR (CDCl3, dTMS) 7.51 (2H, d, 3JHH =9 Hz, m-ArH), 6.69 (2H, d, 3JHH =9 Hz, o-ArH), 3.17 (4H, m), 3.04 (4H, m). 13C NMR (CDCl3) 151.36, 137.73, 118.05, 81.35, 49.92, 45.95.

Workup

  1. customThe solvent was evaporated
  2. washThe organic layer was washed with 100 mL water, 100 mL brine
  3. dry with materialdried over potassium carbonate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-aa3c67212b77468bbdaffa11b14c6ed7
Source dataset
uspto-grants-1996_10
Patent number
US05565449

Linked notes

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