Sodium Iodide → 1,3-dimethyl-6-[4-(N-benzoyl-2-aminoethyl)piperazin-1-yl]-2,4(1H,3H)-pyrimidinedione.hydrochloride

HRID 1729303Notes

Reaction equation

HRID 1729303 reaction equation
[Cl:1][CH2:2][CH2:3][NH:4][C:5](=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH3:13][N:14]1[C:19]([N:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)=[CH:18][C:17](=[O:26])[N:16]([CH3:27])[C:15]1=[O:28].[I-].[Na+].C(N(CC)CC)C>O1CCOCC1>[ClH:1].[CH3:13][N:14]1[C:19]([N:20]2[CH2:25][CH2:24][N:23]([CH2:2][CH2:3][NH:4][C:5](=[O:12])[C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH2:22][CH2:21]2)=[CH:18][C:17](=[O:26])[N:16]([CH3:27])[C:15]1=[O:28]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 101439N-(2-chloroethyl)benzamideHCID 128168731,3-Dimethyl-6-(piperazin-1-yl)pyrimidine-2,4(1H,3H)-dione

Product 1

HCID 190118561,3-dimethyl-6-[4-(N-benzoyl-2-aminoethyl)piperazin-1-yl]-2,4(1H,3H)-pyrimidinedione.hydrochlorideYield 61.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

In 20 ml of dioxane were suspended 2.76 g of N-(2-chloroethyl)benzamide, 1.12 g of 1,3-dimethyl-6-(1-piperazinyl)-2,4(1H,3H)-pyrimidinedione, 3.75 g of sodium iodide and 1.4 ml of triethylamine, and the solution was heated under reflux with stirring for 15 hours. Afterward, the solvent was distilled off, and the resultant residue was dissolved in chloroform, washed with water, and then concentrated to dryness. The residue was purified through a silica gel column chromatograph (chloroform/methanol=100/1 to 100/5 in volume ratio), thereby obtaining 1.25 g of the crystals of 1,3-dimethyl-6-[4-(N-benzoyl-2-aminoethyl)piperazin-1-yl]-2,4(1H,3H)-pyrimidinedione.

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux
  3. distillationAfterward, the solvent was distilled off
  4. dissolutionthe resultant residue was dissolved in chloroform
  5. washwashed with water
  6. concentrationconcentrated to dryness
  7. customThe residue was purified through a silica gel column chromatograph (chloroform/methanol=100/1 to 100/5 in volume ratio)

Sources & evidence

ORD record
ord-a563a6795d6044739a234819ad2257dc
Source dataset
uspto-grants-1994_07
Patent number
US05332739

Reaction notes

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