Water → 1-[3-(1,3-Dimethyl-3,7-dihydro-1H-purine-2,6-dion-7-yl)-2-hydroxypropyl]-4-(3-phenylsulfonylpropyl)piperazine

HRID 1193491Notes

Reaction equation

HRID 1193491 reaction equation
[C:1]1([S:7]([CH2:10][CH2:11][CH2:12]Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.Cl.[CH3:16][N:17]1[C:25](=[O:26])[C:24]2[N:23]([CH2:27][CH:28]([OH:36])[CH2:29][N:30]3[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]3)[CH:22]=[N:21][C:20]=2[N:19]([CH3:37])[C:18]1=[O:38].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:16][N:17]1[C:25](=[O:26])[C:24]2[N:23]([CH2:27][CH:28]([OH:36])[CH2:29][N:30]3[CH2:31][CH2:32][N:33]([CH2:12][CH2:11][CH2:10][S:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)(=[O:9])=[O:8])[CH2:34][CH2:35]3)[CH:22]=[N:21][C:20]=2[N:19]([CH3:37])[C:18]1=[O:38]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 11769949(3-Chloropropanesulfonyl)benzeneHCID 123426901-[3-(1,3-dimethyl-3,7-dihydro-1H-purine-2,6-dion-7-yl)-2-hydroxypropyl]piperazine dihydrochloride

Product 1

HCID 144575191-[3-(1,3-Dimethyl-3,7-dihydro-1H-purine-2,6-dion-7-yl)-2-hydroxypropyl]-4-(3-phenylsulfonylpropyl)piperazine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

0.13 Moles of 3-phenylsulfonyl-1-chloropropane were combined with 0.14 moles of 1-[3-(1,3-dimethyl-3,7-dihydro-1H-purine-2,6-dion-7-yl)-2-hydroxypropyl]piperazine dihydrochloride and 0.3 moles potassium carbonate in 600 grams dimethylformamide. The mixture was stirred overnight at 60° C. After cooling, the reaction mixture was poured into water, extracted with CH2Cl2, washed with water, dried, and evaporated with gentle heating. The residue was recrystallized from ethanol to give the free base form of 1-[3-(1,3-Dimethyl-3,7-dihydro-1H-purine-2,6-dion-7-yl)-2-hydroxypropyl]-4-(3-phenylsulfonylpropyl)piperazine, m.p. 168° C. The dihydrochloride was obtained by adjunction with 12N hydrogen chloride solution as described in Example III, m.p. 190° C.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with CH2Cl2
  3. washwashed with water
  4. customdried
  5. customevaporated with gentle heating
  6. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-9c751f76c1df48deb0836f1ab11515f2
Source dataset
uspto-grants-1989_03
Patent number
US04810706

Reaction notes

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