Triethylamine → 5-Phenyl-5-[4-(2-hydroxyethylidene)piperidinyl]barbituric acid

HRID 993057Notes

Reaction equation

HRID 993057 reaction equation
Br[C:2]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:7](=[O:8])[NH:6][C:5](=[O:9])[NH:4][C:3]1=[O:10].[OH:17][CH2:18][CH:19]=[C:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.C(N(CC)CC)C>C(O)C>[C:11]1([C:2]2([N:23]3[CH2:24][CH2:25][C:20](=[CH:19][CH2:18][OH:17])[CH2:21][CH2:22]3)[C:7](=[O:8])[NH:6][C:5](=[O:9])[NH:4][C:3]2=[O:10])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 108589875-Bromo-5-phenyl-barbiturateHCID 186955332-(Piperidin-4-ylidene)ethan-1-ol

Product 1

HCID 184086515-Phenyl-5-[4-(2-hydroxyethylidene)piperidinyl]barbituric acidYield 16.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-Bromo-5-phenylbarbituric Acid (2.45 g), 4-(hydroxyethylidene)piperidine (1.053 g) and triethylamine (1.15 ml) in 50 ml of ethanol is refluxed for 2 hours. The solvent is evaporated under reduced pressure and the residue is purified by silica gel chromatography (40 g; eluent: ethyl acetate/petroleum ether 8:2), to give 450 mg of the product.

Workup

  1. temperatureis refluxed for 2 hours
  2. customThe solvent is evaporated under reduced pressure
  3. customthe residue is purified by silica gel chromatography (40 g; eluent: ethyl acetate/petroleum ether 8:2)

Sources & evidence

ORD record
ord-a6880f49e0574430a9a9ba2c83271919
Source dataset
uspto-grants-2002_10
Patent number
US06472396B1

Reaction notes

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