1-Benzylpiperazine → HCID 13384070, compound

HRID 371467Notes

Reaction equation

HRID 371467 reaction equation
Br[C:2]1[C:3](=[O:12])[NH:4][C:5](=[O:11])[NH:6][C:7]=1[CH2:8][CH2:9][CH3:10].[F-].[K+].[CH2:15]([N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(O)C>[C:16]1([CH2:15][N:22]2[CH2:23][CH2:24][N:25]([C:2]3[C:3](=[O:12])[NH:4][C:5](=[O:11])[NH:6][C:7]=3[CH2:8][CH2:9][CH3:10])[CH2:26][CH2:27]2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 759941-BenzylpiperazineHCID 522689Potassium FluorideHCID 133840665-Bromo-6-propylpyrimidine-2,4(1H,3H)-dione

Product 1

HCID 13384070HCID 13384070, compoundYield 58.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 53.3 g (0.229 mole) of 5-bromo-6-propyl-2,4(1H,3H)pyrimidinedione and 23.7 g (0.252 mole) of anhydrous potassium fluoride in 176 ml (1.0 mole) of 1-benzylpiperazine was heated under reflux at 140° C. for 14 hours. The reaction mixture was cooled to 80° C. and 100 ml of ethanol was added. The mixture was poured into one liter of ice water. The solid was collected and washed with one liter of water. Recrystallization from ethanol and drying in vacuo at 59° C. for 16 hours gave 44.1 g of the product as an off-white solid; mp 233°-235° C.

Workup

  1. temperaturewas heated
  2. temperatureThe reaction mixture was cooled to 80° C.
  3. customThe solid was collected
  4. washwashed with one liter of water
  5. customRecrystallization from ethanol
  6. customdrying in vacuo at 59° C. for 16 hours

Sources & evidence

ORD record
ord-93e95a1eae524b12b278022f2569e32a
Source dataset
uspto-grants-1985_07
Patent number
US04532240

Reaction notes

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