3-Methylglutaric anhydride → 5-(4-methylpiperazin-1-yl)-5-oxopentanoic acid

HRID 1374584Notes

Reaction equation

HRID 1374584 reaction equation
C[CH:2]1[CH2:8][C:7](=[O:9])[O:6][C:4](=[O:5])[CH2:3]1.[N:10]1([CH:16]2CCCN2CC(O)=O)[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1>O1CCOCC1>[CH3:16][N:10]1[CH2:15][CH2:14][N:13]([C:7](=[O:9])[CH2:8][CH2:2][CH2:3][C:4]([OH:6])=[O:5])[CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 778283-Methylglutaric anhydride2×HCID 69503331HCID 69503331, compound

Product 1

HCID 7068365-(4-methylpiperazin-1-yl)-5-oxopentanoic acidYield 171%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1.6 g of 3-methylglutaric anhydride and then 2.62 g of piperazin-1-ylcarboxymethylpyrrolidine are added to 20 cm3 dioxane. After stirring for 8 hours, an additional 320 mg of 3-methylglutaric anhydride are added and then the stirring is continued at 20° C. for 18 hours. The solvent is evaporated under reduced pressure and then the resulting oil is dried at 45° C. (90 Pa) to give 4.5 g of 5-(4-methylpiperazin-1-yl)-5-oxopentanoic acid in the form of an orange-colored oil which is used as it is.

Workup

  1. waitthe stirring is continued at 20° C. for 18 hours
  2. customThe solvent is evaporated under reduced pressure
  3. customthe resulting oil is dried at 45° C. (90 Pa)

Sources & evidence

ORD record
ord-8c7334a3b72e495db4e9c36ef1211c40
Source dataset
uspto-grants-2007_01
Patent number
US07166594B2

Reaction notes

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