Magnesium → (RS)-5-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-1-phenyl-imidazolidin-2-one

HRID 1864405Notes

Reaction equation

HRID 1864405 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[N:9]1[CH2:14][CH2:13][N:12]([C:15]([CH:17]2[CH2:21][N:20](S(C3C=CC(C)=CC=3)(=O)=O)[C:19](=[O:32])[N:18]2[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[O:16])[CH2:11][CH2:10]1.[Mg]>CO>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[N:9]1[CH2:14][CH2:13][N:12]([C:15]([CH:17]2[N:18]([C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)[C:19](=[O:32])[NH:20][CH2:21]2)=[O:16])[CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 5462224MagnesiumHCID 25027933(RS)-4-[4-(2,5-Dimethyl-phenyl)-piperazine-1-carbonyl]-3-phenyl-1-(toluene-4-sulfonyl)-imidazolidin-2-one

Product 1

HCID 67142096(RS)-5-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-1-phenyl-imidazolidin-2-oneYield 69.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of (RS)-4-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-3-phenyl-1-(toluene-4-sulfonyl)-imidazolidin-2-one (example 10, 0.59 g) and magnesium powder (0.215 g) in methanol (25 ml) was refluxed for 7 h and stirred at room temperature for 18 h. The mixture was filtered and the filtrate was concentrated. The product was purified by chromatography ((SiO2, ethyl acetate=>ethyl acetate/methanol 95:5) to give (RS)-5-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-1-phenyl-imidazolidin-2-one (0.292 g) as a colorless solid.

Workup

  1. temperaturewas refluxed for 7 h
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. customThe product was purified by chromatography ((SiO2, ethyl acetate=>ethyl acetate/methanol 95:5)

Sources & evidence

ORD record
ord-8141cbe76b5e413cb5fbfa038463c2fa
Source dataset
uspto-grants-2009_12
Patent number
US07625902B2

Reaction notes

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