Glutaric anhydride → 4-Ethyl-δ-oxo-1-piperazinepentanoic acid

HRID 1374585Notes

Reaction equation

HRID 1374585 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1)[CH3:2].[C:9]1(=[O:16])[O:15][C:13](=[O:14])[CH2:12][CH2:11][CH2:10]1>O1CCOCC1.C(OCC)C>[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([C:9](=[O:16])[CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])[CH2:5][CH2:4]1)[CH3:2]

Participants

5

Reactant 2

HCID 7940Glutaric anhydrideHCID 791961-Ethylpiperazine

Product 1

HCID 185215744-Ethyl-δ-oxo-1-piperazinepentanoic acidYield 65%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent2×

Procedure

1.5 g of 1-ethylpiperazine and 1.5 g of glutaric anhydride in solution in 5 cm3 of dioxane are added, under argon, to 10 cm3 of dioxane. The stirring is continued at 25° C. for 19 hours. The solvents are evaporated under reduced pressure (2.7 kPa) to give a brown oil which is stirred in ethyl ether. The solid obtained is filtered, rinsed with diethyl ether and then dried at 20° C. (90 Pa) to give 1.95 g of 5-(4-ethylpiperazin-1-yl)-5-oxopentanoic acid in the form of a hygroscopic pink solid which is used as it is.

Workup

  1. customThe solvents are evaporated under reduced pressure (2.7 kPa)
  2. customto give a brown oil which
  3. customThe solid obtained
  4. filtrationis filtered
  5. washrinsed with diethyl ether
  6. customdried at 20° C. (90 Pa)

Sources & evidence

ORD record
ord-134a511cb49d43e69df086bc4cf062a0
Source dataset
uspto-grants-2007_01
Patent number
US07166594B2

Reaction notes

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