HCID 54463805, compound → HCID 10999226, compound

HRID 487339Notes

Reaction equation

HRID 487339 reaction equation
[CH:1](=[C:8]1[NH:13][C:12](=[O:14])[CH:11]([CH2:15][C:16]#[N:17])[NH:10][C:9]1=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>CN(C)C=O.[C].[Pd]>[CH2:1]([CH:8]1[NH:13][C:12](=[O:14])[CH:11]([CH2:15][C:16]#[N:17])[NH:10][C:9]1=[O:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 54463805HCID 54463805, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 10999226HCID 10999226, compoundYield 91.5%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

2.91 g (0.0121 mol) of 3-benzylidene-6-cyanomethyl-2,5-dioxopiperazine was dissolved in 80 ml of dimethylformamide and catalytically reduced with hydrogen at room temperature by adding 1.4 g of 10% palladium carbon. After reaction for 4 hours, the catalyst was removed by filtration, and the resulting filtrate was concentrated to obtained 2.68 g of 3-benzyl-6-cyanomethyl-2,5-dioxopiperazine. Yield: 91.5%. 1H NMR (d6 -DMSO) δ2.13 (dd, 1H), δ2.21 (dd, 1H), δ3.00 (dd, 1H), δ3.14 (dd, 1H), δ4.12 (m, 1H), δ4.29 (m, 1H, δ7.29 (m, 5H), δ8.32 (bs, 1H), δ8.41 (bs, 1H) MS (FAB):244 (MH+) mp:255°-256° C.

Workup

  1. customAfter reaction for 4 hours
  2. customthe catalyst was removed by filtration
  3. concentrationthe resulting filtrate was concentrated

Sources & evidence

ORD record
ord-a74dd99cbbfa4b948e1b4cc8b1655132
Source dataset
uspto-grants-1994_03
Patent number
US05294714

Reaction notes

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