Triethylamine → 5-{2-[4-(2-tert-Butyl-4-methylphenyl)piperazin-1-yl]-2-oxoethyl}imidazolidine-2,4-dione

HRID 534982Notes

Reaction equation

HRID 534982 reaction equation
Cl.Cl.[C:3]([C:7]1[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][C:8]=1[N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1)([CH3:6])([CH3:5])[CH3:4].[O:20]=[C:21]1[NH:25][CH:24]([CH2:26][C:27](O)=[O:28])[C:23](=[O:30])[NH:22]1.C(N(CC)CC)C.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.C([O-])(O)=O.[Na+]>CN(C)C=O>[C:3]([C:7]1[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][C:8]=1[N:14]1[CH2:15][CH2:16][N:17]([C:27](=[O:28])[CH2:26][CH:24]2[NH:25][C:21](=[O:20])[NH:22][C:23]2=[O:30])[CH2:18][CH2:19]1)([CH3:6])([CH3:4])[CH3:5]

Participants

8

Reactant 6

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 95492Hydantoin-5-acetic acidHCID 516892Sodium BicarbonateHCID 667508371-(2-Tert-butyl-4-methylphenyl)piperazine dihydrochloride

Product 1

HCID 667927675-{2-[4-(2-tert-Butyl-4-methylphenyl)piperazin-1-yl]-2-oxoethyl}imidazolidine-2,4-dioneYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-(2-tert-butyl-4-methylphenyl)piperazine dihydrochloride (Reference Example 10, 0.31 g, 1.0 mmol), (2,5-dioxoimidazolidin-4-yl)acetic acid (0.19 g, 1.2 mmol), triethylamine (420 μL, 3.0 mmol), EDCI (0.23 g, 1.2 mmol) and HOBt (0.18 g, 1.2 mmol) in N,N-dimethylformamide (5 mL) was stirred at room temperature for 2 days. The reaction mixture was poured into saturated NaHCO3 solution and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give the title compound (0.33 g, 89%) as a orange solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6eda969acc724286a5005179323c4244
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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