1-(2-Hydroxyethyl)piperazine → 5-[3-(4-Methoxyphenyl)propyl]-5-[4-(2-hydroxyethyl)piperazinyl]barbituric Acid

HRID 993054Notes

Reaction equation

HRID 993054 reaction equation
Br[C:2]1([CH2:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[C:7](=[O:8])[NH:6][C:5](=[O:9])[NH:4][C:3]1=[O:10].[OH:22][CH2:23][CH2:24][N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1>C(O)C>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([CH2:13][CH2:12][CH2:11][C:2]2([N:28]3[CH2:29][CH2:30][N:25]([CH2:24][CH2:23][OH:22])[CH2:26][CH2:27]3)[C:7](=[O:8])[NH:6][C:5](=[O:9])[NH:4][C:3]2=[O:10])=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 76771-(2-Hydroxyethyl)piperazineHCID 184086795-Bromo-5-[3-(4-methoxyphenyl)propyl]barbituric acid

Product 1

HCID 184086745-[3-(4-Methoxyphenyl)propyl]-5-[4-(2-hydroxyethyl)piperazinyl]barbituric AcidYield 3.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A of 5-Bromo-5-[3-(4-Methoxyphenyl)propyl]barbituric Acid (710 mg) and N-(2-hydroxyethyl)piperazine (281 mg) in 25 ml of ethanol is refluxed for 4 hours. The solvent is evaporated under reduced pressure and the residue is partitioned between 1 N hydrochloric acid and ethyl acetate. The aqueous phase is basified to pH=6-7 and extracted with ethyl acetate. The organic phase is concentrated to dryness and the residue is crystallized from ethyl acetate to give 30 mg of the product.

Workup

  1. customThe solvent is evaporated under reduced pressure
  2. customthe residue is partitioned between 1 N hydrochloric acid and ethyl acetate
  3. extractionextracted with ethyl acetate
  4. concentrationThe organic phase is concentrated to dryness
  5. customthe residue is crystallized from ethyl acetate

Sources & evidence

ORD record
ord-06b3964bb09e48b6a4ec998ca2b1d46c
Source dataset
uspto-grants-2002_10
Patent number
US06472396B1

Reaction notes

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