Formaldehyde → 1-(4-Chlorophenyl)-3-(4-(2-methoxyethyl)piperazin-1-yl)methyl-2-pyrrolidinone

HRID 1268374Notes

Reaction equation

HRID 1268374 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH2:11][CH:10]([C:13](O)=O)[C:9]2=[O:16])=[CH:4][CH:3]=1.[CH3:17][O:18][CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.C=O>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH2:11][CH:10]([CH2:13][N:24]3[CH2:25][CH2:26][N:21]([CH2:20][CH2:19][O:18][CH3:17])[CH2:22][CH2:23]3)[C:9]2=[O:16])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 27346381-(2-Methoxyethyl)piperazineHCID 40570841-(4-Chlorophenyl)-2-oxopyrrolidine-3-carboxylic acid

Product 1

HCID 49132091-(4-Chlorophenyl)-3-(4-(2-methoxyethyl)piperazin-1-yl)methyl-2-pyrrolidinoneYield 77.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

3.0 g of 1-(4-chlorophenyl)-3-carboxy-2-pyrrolidinone and 2.32 g of 4-(2-methoxyethyl)piperazine were mixed with 6 ml of methanol. Thereto was added 0.465 g of 80% paraformaldehyde. The mixture was subjected to a reaction for 10.5 hours under refluxing and then cooled to room temperature. Thereto was added 10 ml of methanol, and the insolubles were removed by filtration. The filtrate was concentrated under reduced pressure. The residue was mixed with 15 ml of water. The resulting crystals were collected by filtration and washed with 3 ml of 95% aqueous methanol twice to obtain 3.42 g of 1-(4-chlorophenyl)-3-[4-(2-methoxyethyl)piperazine-1-yl]methyl-2-pyrrolidinone.

Workup

  1. customThe mixture was subjected to a reaction for 10.5 hours
  2. temperatureunder refluxing
  3. customthe insolubles were removed by filtration
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. additionThe residue was mixed with 15 ml of water
  6. filtrationThe resulting crystals were collected by filtration
  7. washwashed with 3 ml of 95% aqueous methanol twice

Sources & evidence

ORD record
ord-0efb4611320d461090330bc0b9808747
Source dataset
uspto-grants-2003_04
Patent number
US06555694B1

Reaction notes

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