1-(2-Hydroxyethyl)piperazine → 5-(4'phenoxyphenyl)-5-[N-(2-hydroxyethyl)piperazinyl]barbituric acid

HRID 993081Notes

Reaction equation

HRID 993081 reaction equation
Br[C:2]1([C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:13][CH:12]=2)[C:7](=[O:8])[NH:6][C:5](=[O:9])[NH:4][C:3]1=[O:10].[OH:24][CH2:25][CH2:26][N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1>CO>[O:17]([C:14]1[CH:15]=[CH:16][C:11]([C:2]2([CH:28]3[CH2:29][NH:30][CH2:31][CH2:32][N:27]3[CH2:26][CH2:25][OH:24])[C:7](=[O:8])[NH:6][C:5](=[O:9])[NH:4][C:3]2=[O:10])=[CH:12][CH:13]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 76771-(2-Hydroxyethyl)piperazineHCID 227322335-Bromo-5-(4'-phenoxyphenyl)barbituric acid

Product 1

HCID 184088295-(4'phenoxyphenyl)-5-[N-(2-hydroxyethyl)piperazinyl]barbituric acidYield 75.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 5-Bromo-5-(4′-phenoxyphenyl)barbituric Acid (50 mg) in 0.2 ml of methanol is added dropwise with a solution of N-(2-hydroxyethyl)piperazine (52 mg) in 0.6 ml of methanol and the mixture is stirred for 2 hours. The white precipitate is recovered by filtration and dried under vacuum at 60° C. overnight. 42.6 mg of the product are obtained, m.p. >240° C. 1H-NMR in d6-DMSO: 2.2-2.45 ppm (m, 6H); 2.55 ppm (m, 4H); 3.45 ppm (m, 2H); 4.4 ppm (t, 1H); 6.9-7.7 ppm (m, 9H); 11.6 ppm (s, 2H).

Workup

  1. filtrationThe white precipitate is recovered by filtration
  2. customdried under vacuum at 60° C. overnight

Sources & evidence

ORD record
ord-460ab6e0218a4e3a867abe07986866ed
Source dataset
uspto-grants-2002_10
Patent number
US06472396B1

Reaction notes

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