N1-(2,6-dimethylphenyl)-4-(phenylmethyl)-1,2-piperazinediacetamide → N1-(2,6-dimethylphenyl)-1,2-piperazinediacetamide

HRID 35326Notes

Reaction equation

HRID 35326 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][C:10](=[O:29])[CH2:11][N:12]1[CH2:17][CH2:16][N:15](CC2C=CC=CC=2)[CH2:14][CH:13]1[CH2:25][C:26]([NH2:28])=[O:27].[H][H]>[Pd].CO>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][C:10](=[O:29])[CH2:11][N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH:13]1[CH2:25][C:26]([NH2:28])=[O:27]

Participants

5

Reactant 2

HCID 21295628N1-(2,6-dimethylphenyl)-4-(phenylmethyl)-1,2-piperazinediacetamideHCID 178418361HCID 178418361, compound

Product 1

HCID 14230226N1-(2,6-dimethylphenyl)-1,2-piperazinediacetamideYield 97.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 12.8 parts of N1 -(2,6-dimethylphenyl)-4-(phenylmethyl)-1,2-piperazinediacetamide and 120 parts of methanol was hydrogenated at normal pressure and at room temperature with 2 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated. The oily residue was crystallized from acetonitrile, yielding 7.7 parts (97.5%) of N1 -(2,6-dimethylphenyl)-1,2-piperazinediacetamide; mp. 171.9° C. (intermediate 72).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customThe oily residue was crystallized from acetonitrile

Sources & evidence

ORD record
ord-441336eb44074caab8917dfa56eaf7c7
Source dataset
uspto-grants-1988_08
Patent number
US04766125

Reaction notes

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