Triethylamine → HCID 19011879, compound

HRID 1729310Notes

Reaction equation

HRID 1729310 reaction equation
[CH3:1][N:2]1[C:7]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][OH:17])[CH2:10][CH2:9]2)=[CH:6][C:5](=[O:18])[N:4]([CH3:19])[C:3]1=[O:20].C(N(CC)CC)C.[Cl:28][C:29]1[CH:37]=[CH:36][C:32]([C:33](Cl)=[O:34])=[CH:31][CH:30]=1>O1CCOCC1>[ClH:28].[CH3:1][N:2]1[C:7]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][O:17][C:33](=[O:34])[C:32]3[CH:36]=[CH:37][C:29]([Cl:28])=[CH:30][CH:31]=3)[CH2:10][CH2:9]2)=[CH:6][C:5](=[O:18])[N:4]([CH3:19])[C:3]1=[O:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 85014-Chlorobenzoyl chlorideHCID 103564171,3-dimethyl-6-[4-(3-hydroxypropyl)piperazin-1-yl]-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 19011879HCID 19011879, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

In 50 ml of dioxane were dissolved 1.45 g of 1,3-dimethyl-6-[4-(3-hydroxypropyl)piperazin-1-yl]-2,4(1H,3H)-pyrimidinedione and 1.5 ml of triethylamine, and 10 ml of a dioxane solution containing 1.05 g of 4-chlorobenzoyl chloride was further added dropwise. The solution was stirred at 50°-60° C. for 2 hours, and the solvent was then distilled off. Afterward, 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 100/3 in volume ratio), thereby obtaining 1.21 g of the crystals of 1,3-dimethyl-6-[4-(3-[4-chlorobenzoyloxy]propyl)piperazin-1-yl]-2,4(1H,3H)-pyrimidinedione.

Workup

  1. additionwas further added dropwise
  2. distillationthe solvent was then distilled off
  3. dissolutionAfterward, the resultant residue was dissolved in chloroform
  4. washwashed with water
  5. concentrationconcentrated to dryness
  6. customThe residue was purified through a silica gel column chromatograph (chloroform/methanol=100/1 to 100/3 in volume ratio)

Sources & evidence

ORD record
ord-52ce8556d2764a0eae13d987b912f1ac
Source dataset
uspto-grants-1994_07
Patent number
US05332739

Reaction notes

Loading…