L-Pyroglutamic Acid → 5-[[4-[2-(4-Morpholinyl)-2-oxoethyl]-1-piperazinyl]carbonyl]-2-pyrrolidinone

HRID 1029397Notes

Reaction equation

HRID 1029397 reaction equation
[NH:1]1[C:5](=[O:6])[CH2:4][CH2:3][C@H:2]1[C:7]([OH:9])=O.[O:10]1[CH2:15][CH2:14][N:13]([C:16]([CH2:18][N:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)=[O:17])[CH2:12][CH2:11]1.C1CCC(N=C=NC2CCCCC2)CC1>C(#N)C>[O:10]1[CH2:15][CH2:14][N:13]([C:16]([CH2:18][N:19]2[CH2:20][CH2:21][N:22]([C:7]([CH:2]3[NH:1][C:5](=[O:6])[CH2:4][CH2:3]3)=[O:9])[CH2:23][CH2:24]2)=[O:17])[CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 7405L-Pyroglutamic AcidHCID 10868DicyclohexylcarbodiimideHCID 1006221-(Morpholinocarbonylmethyl)piperazine

Product 1

HCID 140536945-[[4-[2-(4-Morpholinyl)-2-oxoethyl]-1-piperazinyl]carbonyl]-2-pyrrolidinoneYield 93.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Pyroglutamic acid (1.6 g), 2.1 g of 1-(morpholinocarbonylmethyl)piperazine, 2.47 g of DCC and 130 ml of acetonitrile were heated to reflux for 48 hours with stirring. The insoluble matter was removed by filtering the reaction mixture and the solvent was evaporated from the filtrate in vacuo. The residue was subjected to a silica gel column chromatography to give 3.0 g of the product. This was recrystallized from a mixture of ethyl acetate, isopropanol and n-hexane to give 2.6 g of desired product, m.p. 167°-169° C.

Workup

  1. temperatureto reflux for 48 hours
  2. customThe insoluble matter was removed
  3. filtrationby filtering the reaction mixture
  4. customthe solvent was evaporated from the filtrate in vacuo

Sources & evidence

ORD record
ord-f529f40e8bae4bf796159c65f8c468db
Source dataset
uspto-grants-1992_04
Patent number
US05102882

Reaction notes

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