Iodine → 1-(4-Iodophenyl)piperazine

HRID 1655690Notes

Reaction equation

HRID 1655690 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, 0.034 mol) were added in portions to a magnetically stirred solution of 5 grams of 1-phenylpiperazine in 80 mL acetic acid. The mixture stirred for 1 hour. 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 was used 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). 13 C 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-95addbfad8f140e3bc36f599a8205d0d
Source dataset
uspto-grants-1993_10
Patent number
US05250679

Reaction notes

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