Triethylamine → 5-{2-[4-(2-Tert-butylphenyl)piperazin-1-yl]-2-oxoethyl}imidazolidine-2,4-dione

HRID 534950Notes

Reaction equation

HRID 534950 reaction equation
Cl.Cl.[C:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)([CH3:6])([CH3:5])[CH3:4].[O:19]=[C:20]1[NH:24][CH:23]([CH2:25][C:26](O)=[O:27])[C:22](=[O:29])[NH:21]1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.[Cl-].[NH4+]>CN(C=O)C>[C:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[CH2:18][CH2:17][N:16]([C:26](=[O:27])[CH2:25][CH:23]2[NH:24][C:20](=[O:19])[NH:21][C:22]2=[O:29])[CH2:15][CH2:14]1)([CH3:6])([CH3:4])[CH3:5]

Participants

8

Reactant 6

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 95492Hydantoin-5-acetic acidHCID 667511491-(2-Tert-butylphenyl)piperazine dihydrochloride

Product 1

HCID 667510355-{2-[4-(2-Tert-butylphenyl)piperazin-1-yl]-2-oxoethyl}imidazolidine-2,4-dioneYield 70.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 1-(2-tert-butylphenyl)piperazine dihydrochloride (Reference Example 1, 0.400 g, 1.37 mmol), (2,5-dioxoimidazolidin-4-yl)acetic acid (0.261 g, 1.65 mmol), EDCI (0.311 g, 1.65 mmol), HOBt (0.223 g, 1.65 mmol) and triethylamine (496 μl, 3.56 mmol) in DMF (13 mL) was stirred at room temperature for 16 h. The reaction mixture was poured into saturated ammonium chloride solution and extracted with ethyl acetate. The organic layer was washed with saturated sodium hydrogen carbonate solution and brine, dried over MgSO4, and the solvent was evaporated under reduced pressure to give crude product. The product was purified by re-crystallization from THF and n-hexane to provide 5-{2-[4-(2-tert-butylphenyl)piperazin-1-yl]-2-oxoethyl}imidazolidine-2,4-dione (0.344 g, 70%) as a white powder.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated sodium hydrogen carbonate solution and brine
  3. dry with materialdried over MgSO4
  4. customthe solvent was evaporated under reduced pressure
  5. customto give crude product
  6. customThe product was purified by re-crystallization from THF and n-hexane

Sources & evidence

ORD record
ord-8508b38d5eba41a78166e67ef91be6d5
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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