Hydrochloric Acid → HCID 20061198, compound

HRID 1085273Notes

Reaction equation

HRID 1085273 reaction equation
C(O)(=O)C(O)=O.[CH3:7][N:8]1[C:13]([N:14]2[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][CH2:22][O:23][C:24]3[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][C:25]=3[C:33]([O:35]C)=[O:34])[CH2:16][CH2:15]2)=[CH:12][C:11](=[O:37])[N:10]([CH3:38])[C:9]1=[O:39].[OH-].[Na+].Cl>CO>[CH3:7][N:8]1[C:13]([N:14]2[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][CH2:22][O:23][C:24]3[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][C:25]=3[C:33]([OH:35])=[O:34])[CH2:16][CH2:15]2)=[CH:12][C:11](=[O:37])[N:10]([CH3:38])[C:9]1=[O:39]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 20061320HCID 20061320, compound2×

Product 1

HCID 20061198HCID 20061198, compoundYield 103.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.38 g of 1,3-dimethyl-6-{4-[3-(2-methoxycarbonyl-4-nitrophenyloxy)propyl]piperazin-1-yl}-2,4(1H,3H)-pyrimidinedione (Compound 151--free form) were dissolved in 200 ml of methanol, followed by the addition of 100 ml of a 1.5 N aqueous solution of sodium hydroxide. The resultant mixture was stirred at 60° C. for 30 minutes. The reaction mixture was allowed to cool down, neutralized with dilute hydrochloric acid, and then concentrated to a total volume of 50 ml under reduced pressure. The concentrate was ice-cooled and precipitated crystals were collected by filtration, thereby obtaining 1.16 g of 1,3-dimethyl-6-{4-[3-(2-carboxy-4-nitrophenyloxy)propyl]piperazin-1-yl}-2,4(1H,3H)-pyrimidinedione.

Workup

  1. temperatureto cool down
  2. concentrationconcentrated to a total volume of 50 ml under reduced pressure
  3. temperaturecooled
  4. customprecipitated crystals
  5. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-8dbdfc224d8440a79fd77148b880cca8
Source dataset
uspto-grants-1991_04
Patent number
US05008267

Reaction notes

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