Potassium Carbonate → 5-[[4-[2-(4-Morpholinyl)-2-oxoethyl]-1-piperazinyl]carbonyl]-2-pyrrolidinone

HRID 1029398Notes

Reaction equation

HRID 1029398 reaction equation
[NH:1]1[CH:5]([C:6]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[O:7])[CH2:4][CH2:3][C:2]1=[O:14].Cl[CH2:16][C:17]([N:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1)=[O:18].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[O:22]1[CH2:23][CH2:24][N:19]([C:17]([CH2:16][N:11]2[CH2:10][CH2:9][N:8]([C:6]([CH:5]3[NH:1][C:2](=[O:14])[CH2:3][CH2:4]3)=[O:7])[CH2:13][CH2:12]2)=[O:18])[CH2:20][CH2:21]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 74040Morpholine, 4-(chloroacetyl)-HCID 140536931-(2-Pyrrolidone-5-carbonyl)piperazine

Product 1

HCID 140536945-[[4-[2-(4-Morpholinyl)-2-oxoethyl]-1-piperazinyl]carbonyl]-2-pyrrolidinoneYield 93.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(2-Pyrrolidone-5-carbonyl)piperazine (3.7 g), 3.7 g of 4-chloroacetylmorpholine, 4.4 g of anhydrous potassium carbonate, and 20 ml of N,N-dimethylformamide were stirred at 70°-75° C. for 1 hour. The insoluble matter was removed by filtering the reaction mixture, the solvent was removed by evaporating the filtrate, and the residue was purified by a silica gel column chromatography to give 5.7 g of the product. This was recrystallized from a mixture of ethanol, ethyl acetate and diethyl ether to give 4.2 g of desired product, m.p. 167°-169° C.

Workup

  1. customThe insoluble matter was removed
  2. filtrationby filtering the reaction mixture
  3. customthe solvent was removed
  4. customby evaporating the filtrate
  5. customthe residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-48996c9e0a944efe9ea566a393545754
Source dataset
uspto-grants-1992_04
Patent number
US05102882

Reaction notes

Loading…