1-Benzylpiperazine → HCID 13066325, compound

HRID 2166348Notes

Reaction equation

HRID 2166348 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][C:8]([O:10]N1C(=O)CCC1=O)=O.[CH2:18]([N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C)C=O.C(OCC)(=O)C>[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][C:8]([N:28]1[CH2:29][CH2:30][N:25]([CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:26][CH2:27]1)=[O:10]

Participants

5

Reactant 2

HCID 759941-BenzylpiperazineHCID 23039541HCID 23039541, compound

Product 1

HCID 13066325HCID 13066325, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 14.4 g (60 mmol) of N-[2-(2-oxopyrrolidin-1-yl)-acetoxy]-succinimide and 10.6 g (60 mmol) of 1-benzylpiperazine in 125 ml of dimethylformamide is stirred for 16 hours at 20°. The reaction mixture is concentrated to dryness by evaporation under reduced pressure at 90°. The oily residue is taken up in 250 ml of water, and a solution of 5.4 g of oxalic acid in 5 ml of water is added, and then the whole is stirred in an ice bath. The resulting crystalline oxalate is filtered off with suction, dissolved in 400 ml of water and the pH is adjusted to 9 with concentrated ammonia solution The clear aqueous solution is washed twice with 30 ml of ether each time, the ethereal extracts are discarded and the aqueous layer is concentrated by evaporation under reduced pressure at 70°. The residue is composed of a sticky mass which is stirred into 400 ml of ethanol at 30° and the insoluble matter is filtered off with suction. After concentrating the clear ethanolic filtrate by evaporation, a slightly yellowish oil is obtained. This is boiled in 130 ml of ethyl acetate and filtered while hot, and the filtrate is stirred in an ice bath to complete the reaction. The precipitated crystals are filtered off with suction and dried on a water bath. 1-[2-(2-oxopyrrolidin-1-yl)-acetyl]-4-benzylpiperazine is obtained.

Workup

  1. concentrationThe reaction mixture is concentrated to dryness by evaporation under reduced pressure at 90°
  2. additiona solution of 5.4 g of oxalic acid in 5 ml of water is added
  3. filtrationThe resulting crystalline oxalate is filtered off with suction
  4. dissolutiondissolved in 400 ml of water
  5. washis washed twice with 30 ml of ether each time
  6. concentrationthe aqueous layer is concentrated by evaporation under reduced pressure at 70°
  7. stirringis stirred into 400 ml of ethanol at 30°
  8. filtrationthe insoluble matter is filtered off with suction
  9. concentrationAfter concentrating the clear ethanolic filtrate
  10. customby evaporation
  11. customa slightly yellowish oil is obtained
  12. filtrationfiltered while hot, and the filtrate
  13. stirringis stirred in an ice bath
  14. customthe reaction
  15. filtrationThe precipitated crystals are filtered off with suction
  16. customdried on a water bath

Sources & evidence

ORD record
ord-93718a1ece4d49dea7050c8054137c8c
Source dataset
uspto-grants-1990_07
Patent number
US04945092

Reaction notes

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