1-(4-Chlorophenyl)piperazine → {2-[4-(4-chlorophenyl)piperazin-1-yl]-5,5-dioxo-6,7-dihydro-5H-5lambda6-thieno[3,2-d]pyrimidin-4-yl}propylamine

HRID 2240117Notes

Reaction equation

HRID 2240117 reaction equation
Cl[C:2]1[N:3]=[C:4]([CH2:13][CH2:14][CH2:15][NH2:16])[C:5]2[S:10](=[O:12])(=[O:11])[CH2:9][CH2:8][C:6]=2[N:7]=1.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)=[CH:20][CH:19]=1>O1CCOCC1>[Cl:17][C:18]1[CH:19]=[CH:20][C:21]([N:24]2[CH2:29][CH2:28][N:27]([C:2]3[N:3]=[C:4]([CH2:13][CH2:14][CH2:15][NH2:16])[C:5]4[S:10](=[O:12])(=[O:11])[CH2:9][CH2:8][C:6]=4[N:7]=3)[CH2:26][CH2:25]2)=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 974781-(4-Chlorophenyl)piperazineHCID 86616274(2-chloro-5,5-dioxo-6,7-dihydro-5H-5lambda6-thieno[3,2-d]pyrimidin-4-yl)propylamine

Product 1

HCID 68675324{2-[4-(4-chlorophenyl)piperazin-1-yl]-5,5-dioxo-6,7-dihydro-5H-5lambda6-thieno[3,2-d]pyrimidin-4-yl}propylamineYield 70%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

0.262 g (1.00 mmol) of (2-chloro-5,5-dioxo-6,7-dihydro-5H-5λ6-thieno[3,2-d]pyrimidin-4-yl)propylamine (II) and 0.433 g (2.20 mmol) of 1-(4-chlorophenyl)piperazine are placed in 4.50 mL of dioxane, then heated to 150° C. in the microwave for 0.75 hours. Then the reaction mixture is concentrated by evaporation, the residue is treated with water. It is suction filtered, washed with water, and dried. The product which is not yet clean is purified by chromatography (column: 10 g Chromabond SiOH cartridge, solvent: petroleum ether/ether 1:1). Corresponding fractions are combined and concentrated by evaporation. 0.295 g of product III (70%) is obtained as a powder (m.p. 243° C.-245° C.).

Workup

  1. concentrationThen the reaction mixture is concentrated by evaporation
  2. additionthe residue is treated with water
  3. filtrationfiltered
  4. washwashed with water
  5. customdried
  6. customThe product which is not yet clean is purified by chromatography (column: 10 g Chromabond SiOH cartridge, solvent: petroleum ether/ether 1:1)
  7. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-ffde509e217447dda654456e71f51e09
Source dataset
uspto-grants-2010_05
Patent number
US07723341B2

Reaction notes

Loading…