2,4-Imidazolidinedione, 5-(4-nitrophenyl)-5-phenyl-3-(3-(4-phenyl-1-piperidinyl)propyl)- → 2,4-Imidazolidinedione, 5-(4-aminophenyl)-5-phenyl-3-(3-(4-phenyl-1-piperidinyl)propyl)-

HRID 435815Notes

Reaction equation

HRID 435815 reaction equation
[C:1]1([CH:7]2[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][CH2:15][N:16]3[C:20](=[O:21])[C:19]([C:28]4[CH:33]=[CH:32][C:31]([N+:34]([O-])=O)=[CH:30][CH:29]=4)([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[NH:18][C:17]3=[O:37])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H][H]>C(O)(=O)C.[Pd]>[C:1]1([CH:7]2[CH2:8][CH2:9][N:10]([CH2:13][CH2:14][CH2:15][N:16]3[C:20](=[O:21])[C:19]([C:28]4[CH:29]=[CH:30][C:31]([NH2:34])=[CH:32][CH:33]=4)([C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)[NH:18][C:17]3=[O:37])[CH2:11][CH2:12]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 30437362,4-Imidazolidinedione, 5-(4-nitrophenyl)-5-phenyl-3-(3-(4-phenyl-1-piperidinyl)propyl)-HCID 178418361HCID 178418361, compound

Product 1

HCID 30437372,4-Imidazolidinedione, 5-(4-aminophenyl)-5-phenyl-3-(3-(4-phenyl-1-piperidinyl)propyl)-

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

3-[3-(4-phenyl-1-piperidyl) propyl]-5-(4-nitrophenyl)-5-phenylhydantoin (17.5 g, 0.035 mole) in 200 ml of glacial acetic acid and 0.6 g of Pd/C (10%) was reduced on the Parr shaker. The theoretical amount of hydrogen was taken up. The mixture was filtered and concentrated. The concentrate in aqueous methanol was made basic with NH4OH. The solid was recrystallized from aqueous dimethylformamide-methanol and twice from aqueous dioxane.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. concentrationThe concentrate in aqueous methanol
  4. customThe solid was recrystallized from aqueous dimethylformamide-methanol and twice from aqueous dioxane

Sources & evidence

ORD record
ord-1c493d668e994ff9935c85d641893eb7
Source dataset
uspto-grants-1977_02
Patent number
US04006232

Reaction notes

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