Triethylamine → 6-[4-(3-phenoxypropyl)piperazin-1-yl]-2,4(1H,3H)-pyrimidinedione

HRID 1729296Notes

Reaction equation

HRID 1729296 reaction equation
[O:1]([CH2:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[C:25]1[NH:30][C:29](=[O:31])[NH:28][C:27](=[O:32])[CH:26]=1>O1CCOCC1>[O:1]([CH2:8][CH2:9][CH2:10][N:11]1[CH2:12][CH2:13][N:14]([C:25]2[NH:30][C:29](=[O:31])[NH:28][C:27](=[O:32])[CH:26]=2)[CH2:15][CH2:16]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 732726-ChlorouracilHCID 27603511-(3-Phenoxypropyl)piperazine

Product 1

HCID 190118256-[4-(3-phenoxypropyl)piperazin-1-yl]-2,4(1H,3H)-pyrimidinedioneYield 75.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1.1 g of 1-(3-phenoxypropyl)piperazine, 0.8 ml of triethylamine and 0.59 g of 6-chloro-2,4(1H,3H)-pyrimidinedione were dissolved in 15 ml of dioxane, followed by heating under reflux for 1 hour. After cooling, the precipitated crystals were collected by filtration, and then washed with water and hot ethanol to obtain 1.0 g (yield 66% ) of 6-[4-(3-phenoxypropyl)piperazin-1-yl]-2,4(1H,3H)-pyrimidinedione.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 1 hour
  3. temperatureAfter cooling
  4. filtrationthe precipitated crystals were collected by filtration
  5. washwashed with water and hot ethanol

Sources & evidence

ORD record
ord-ca0ba6f5301846ab90e32b71b35b80a0
Source dataset
uspto-grants-1994_07
Patent number
US05332739

Reaction notes

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