Hydrochloric Acid → 1-Phenyl-3-(piperidin-4-yl)imidazolidin-2-one

HRID 1855997Notes

Reaction equation

HRID 1855997 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH2:18][CH2:17][N:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:15]2=[O:25])[CH2:10][CH2:9]1)C1C=CC=CC=1.O.Cl.[H][H]>CO.[Pd]>[NH:8]1[CH2:9][CH2:10][CH:11]([N:14]2[CH2:18][CH2:17][N:16]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:15]2=[O:25])[CH2:12][CH2:13]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 155726681-(1-Benzylpiperidin-4-yl)-3-phenylimidazolidin-2-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 205401631-Phenyl-3-(piperidin-4-yl)imidazolidin-2-oneYield 93.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

11.1 g of 1-(1-benzyl-4-piperidinyl)-3-phenyl-2-imidazolidinone are dissolved in 85 ml of methanol, 34 ml of water and 3.2 ml of hydrochloric acid (chemically pure), and, with the addition of 1.2 g of a 5% palladium on charcoal catalyst, hydrogenated at room temperature and under normal pressure. The calculated amount of hydrogen has been taken up after approx. 15 hours. The reaction mixture is filtered to remove the catalyst and concentrated in a water jet vacuum. The crystalline residue is treated with 2 N sodium carbonate solution and extracted with chloroform. The combined chloroform extracts are dried over sodium sulphate and concentrated in a water jet vacuum to yield 7.6 g of 1-(4-piperidinyl)-3-phenyl-2-imidazolidinone as a colourless oil which crystallises on standing; melting point 123°-124° C.

Workup

  1. customhydrogenated at room temperature
  2. filtrationThe reaction mixture is filtered
  3. customto remove the catalyst
  4. concentrationconcentrated in a water jet vacuum
  5. additionThe crystalline residue is treated with 2 N sodium carbonate solution
  6. extractionextracted with chloroform
  7. dry with materialThe combined chloroform extracts are dried over sodium sulphate
  8. concentrationconcentrated in a water jet vacuum

Sources & evidence

ORD record
ord-276612178dd9454f9c855744afd2a94f
Source dataset
uspto-grants-1980_08
Patent number
US04217350

Reaction notes

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